Category: 18087-73-5

Application of 18087-73-5,Some common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis of compound 10 (0053) 3-bromoimidazo[1,2-b]pyridazine (compound 9: 10 g, 0.05 mol) was dissolved in acetonitrile (100 ml), under protection of nitrogen, trans-dichlorobis(triphenylphosphine)palladium(II) (1.0 g, 1.4 mmol), cuprous iodide (0.3 g, 1.4 mmol), and dicyclohexylamine (11 ml, 0.06 mol) were added, rise the temperature to 80 C, then trimethylsilyl acetylene (8 ml, 0.6 mol) was added slowly into reaction solution, react for 1 hour, detect with TLC, cool down the reaction solution to room temperature, filter the solution, wash the solid with dichloromethane (200 ml), collect the organic phase, evaporate the solvent, add the residue into dichloromethane (100 ml), wash the organic phase with saturated sodium chloride solution (20 ml x2), dry with anhydrous sodium sulfate, evaporate the solvent for the product. Crystallize the product with ethyl acetate/petroleum ether, to give the black powder solid(compound 10:8.9 g, 81.8% yield). (0054) 1HNMR (CDCl3, 400 MHz) delta: 8.47 (dd, J=1.6, 4.4 Hz, 1H), 7.99(s, 1H), 7.96 (dd, J=1.6, 9.2 Hz, 1H), 7.10 (dd, J=4.4, 9.2 Hz, 1H), 0.33 (s, 9H).

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu University; ZHENG, Zhebin; (36 pag.)EP3133069; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18087-73-5, HPLC of Formula: C6H4BrN3

Add 3-bromoimidazo [1,2-b] pyridazine (9.9g, 0.05mol), Pd (pph3) 4 (2.89g, 2.5mmol), vinylboronic acid pinacol ester (8.47g, 0.055mol) And Na2CO3 solution (2M) (23mL, 0.05mol) were added to 1,4-dioxane (150mL). Under nitrogen protection, the temperature was raised to 100 C for 1h, and the reaction solution was poured into 200mL saturated NH4Cl aqueous solution, acetic acid. The organic phase was extracted with ethyl acetate (100 mL × 3), the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The product was isolated by column chromatography on silica gel to obtain 5.1 g of the product, with a yield of 70.5%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Liaoning University; Chen Ye; Liu Ju; Ding Shi; Li Jun; Liu Yutong; Shi Jiantao; Li Jie; Zhou Ziyun; Zhang Jiaojiao; Gong Yilin; (42 pag.)CN110372705; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 18087-73-5, A common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a 100 ml two port in round bottomed flask, adding 3 – bromo imidazole [1, 2 – b] pyridazine (compound 11) (1g, 5.05mmol), Zn (CF3 SO2 )2 (5.0g,15 . 15mmol), 20 ml CH2 Cl2 , 8 ml H2 O. A system is cooled to 0 C after, slowly dropping t – BuOOH (2.5 ml, 25 . 2mmol) dichloro solution 5 ml. Then completing, maintain 0 C, stirring 3h after, the system moving to room temperature stirring 10h, TLC monitoring reaction process, after completion of the reaction, NaHCO adds by drops full and3 Solution to the system does not produce the bubble as the to. Add dichloromethane extraction, the combined organic phase, anhydrous Na2 SO4 Drying, and the pressure of the coils after silica gel, separation and purification through silica gel column (petroleum ether: ethyl acetate=20:1) to obtain compound 12 (0.13g, yield: 10%), compound 13 (0.40g, yield 30%).

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin International Bio-pharmaceutical Joint Institute; Rao Zihe; Bai Cuigai; Chen Yue; Yang Cheng; Wang Lei; Zhong Chuanke; Li Huiying; Sun Tao; Li Jingpei; Wang Yang; (45 pag.)CN106883234; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18087-73-5, HPLC of Formula: C6H4BrN3

To a 30 ml tube was added 3-ethynyl-4-methyl-N- [4- (4-methylpiperazin-1-ylmethyl) -3-trifluoromethylPhenyl] benzamide (126 mg, 0.3 mm & lt; 1 & gt;), 3 & lt; / RTI & gt; bromomethine [1,2_b] U daxazine (59 mg, 0.3 mmo 1), Pd (PPh3)(1 mg, 0.015 mmol), CuI (6 mg, 0.03 mmol), PCy3 (8 mg, 0.015 mmol), Cs2C0 (99 mg, 0.3 mmol)DMFlOml, replaced with argon for 5 minutes and then stirred at 80 C for 8 hours. With ethyl acetate (15 ml x 4), saturated with NaClSolution (30 ml). The organic layers were combined and dried over anhydrous Na2S04. The organic solution was concentrated under reduced pressure and the residue was passed throughThe title compound was obtained in a yield of 79%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NANJING SANHOME PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; CHEN, HONGYAN; ZHANG, DI; XU, XIN; ZHANG, CANG; ZHANG, HONGXING; (9 pag.)CN103664951; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 18087-73-5, The chemical industry reduces the impact on the environment during synthesis 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

A solution of bromo compound (100 mg, 0.510 mmol, 1 equiv), Pd(PPh3)2Cl2 (10 mol%), Cul (5 mol%) and Triphenylphosphine (13.1 mg, 0.05 mmol, 10 mol%) in triethylamine (1.5 mL, 10.78 mmol, 21.1 equiv) was deoxygenated using argon gas. A deoxygenated solution of alkyne (254.6 mg, 0.612 mmol, 1.2 equiv) in DMF (4 mL) was slowly added over 10 minutes. The reaction was then moved to 50 C and allowed to run for 15 hrs. The reaction was the cooled to room temperature, diluted with ethyl acetate (150 mL) and washed with water (5 x 50 mL) and brine (1 x 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, concentrated in vacuo and purified via column chromatography. Yield: 104.5mg, 38.4 % [0197] 1H NMR (500 MHz, DMSO-76) d 10.69 (s, 1H), 8.99 (d, J = 2.2 Hz, 1H), 8.73 (dd, J = 4.3, 2.2 Hz, 1H), 8.49 (d, j = 2.3 Hz, 1H), 8.28 – 8.24 (m, 2H), 8.19 (d, j= 2.5 Hz, 1H), 8.04 (d, j= 8.4 Hz, 1H), 7.70 (d, j= 8.5 Hz, 1H), 7.40 (ddd, j= 9.1, 4.5, 1.9 Hz, 1H), 3.56 (s, 2H), 2.80 (s, 3H), 2.41 (s, 8H), 2.21 (s, 3H). 13C NMR (126 MHz, DMS0 ) d 163.8, 162.7, 148.4, 145.6, 140.3, 139.1, 138.4, 137.7, 132.8, (0234) 131.8, 128.0, 127.8, 126.7, 124.0, 119.8, 117.8, 111.8, 95.2, 83.7, 57.8, 55.0, 52.8, (0235) 45.8, 40.5, 40.3, 40.2, 40.0, 39.8, 39.7, 39.5, 24.0.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromoimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PURDUE RESEARCH FOUNDATION; SINTIM, Herman O.; LAROCQUE, Elizabeth; NAGANNA, N; (98 pag.)WO2020/53812; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 18087-73-5,Some common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis of compound 10 (0053) 3-bromoimidazo[1,2-b]pyridazine (compound 9: 10 g, 0.05 mol) was dissolved in acetonitrile (100 ml), under protection of nitrogen, trans-dichlorobis(triphenylphosphine)palladium(II) (1.0 g, 1.4 mmol), cuprous iodide (0.3 g, 1.4 mmol), and dicyclohexylamine (11 ml, 0.06 mol) were added, rise the temperature to 80 C, then trimethylsilyl acetylene (8 ml, 0.6 mol) was added slowly into reaction solution, react for 1 hour, detect with TLC, cool down the reaction solution to room temperature, filter the solution, wash the solid with dichloromethane (200 ml), collect the organic phase, evaporate the solvent, add the residue into dichloromethane (100 ml), wash the organic phase with saturated sodium chloride solution (20 ml x2), dry with anhydrous sodium sulfate, evaporate the solvent for the product. Crystallize the product with ethyl acetate/petroleum ether, to give the black powder solid(compound 10:8.9 g, 81.8% yield). (0054) 1HNMR (CDCl3, 400 MHz) delta: 8.47 (dd, J=1.6, 4.4 Hz, 1H), 7.99(s, 1H), 7.96 (dd, J=1.6, 9.2 Hz, 1H), 7.10 (dd, J=4.4, 9.2 Hz, 1H), 0.33 (s, 9H).

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu University; ZHENG, Zhebin; (36 pag.)EP3133069; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 18087-73-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 13 (2.5 g, 6.3 mmol) was added in 30 mL dioxane and 6 mL water, and the reaction stirred to dissolve. Then 3-bromo-imidazo [1,2-b] pyridazine (2.5 g, 12.6 mmol) , tetrakis (triphenylphosphine) palladium (0.73 g, 0.63 mmol), sodium carbonate (2.67 g, 25.2 mmol) were added into the reaction solution and refluxed under argon. The reaction was finished within 7 to 10 hours with TLC detection of the reaction progress. After cooled to room temperature, the reaction mixture was filtered through Celite, and the solvent was removal under reduced pressure and the residue was purified by column chromatography: gel (eluent petroleum ether / ethyl acetate). A pale yellow solid, yield: 65%. 1H NMR (DMSO-d6, 400 MHz, delta ppm): 9.53 (s, 1H), 8.69 (s, 1H), 8.66 (d, J = 4.4 Hz, 1H), 8.45 (s, 1H), 8.21 (dd, J = 13.8, 6.9 Hz, 2H), 7.66 (s, 1H), 7.42 (d, J = 8.4 Hz, 1H), 7.31 – 7.24 (m, 2H), 2.20 (s, 3H), 1.48 (s, 8H). ESI-MS m/z : 391.2 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromoimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Liming; Cao, Tingting; Lv, Yongjuan; Ding, Yiming; Yang, Leifu; Zhang, Qiang; Guo, Mingzhou; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5830 – 5835;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 18087-73-5,Some common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Unit Operation 1.1: 1 Sonogashira Reaction AP24595, palladium tetrakis triphenylphosphine (Pd(PPh3)4) , copper (I) iodide (Cul), triethylamine, and tetrahydrofuran (THF) are charged to the reactor. The mixture is stirred and degassed with nitrogen and then pre-degassed AP28141 is charged. The resulting mixture is brought to 45 – 55C and held for not less than 3 hours. The reaction completion is determined by IPC-1 (HPLC). If the IPC-1 criterion is met, the mixture is concentrated to a target volume and cooled. Unit Operation 1.2: Deprotection / 2nd Sonogashira Reaction AP25570, additional palladium tetrakis triphenylphosphine (Pd(PPh3)4), copper (I) iodide (Cul), and tetrahydrofuran (THF) are charged to the reactor. The mixture is concentrated and the water content is determined by IPC-2 (KF). If the IPC-2 criterion is met, the mixture is warmed to 45 – 60C and 25% sodium methoxide solution in methanol is slowly added. The reaction mixture is stirred and held for 30 – 60 minutes at 45 – 55C. The reaction progress is determined by IPC-3 (HPLC). The reaction mixture may be held at a lower temperature during the IPC analysis. If the IPC-3 criterion is met, the process is continued to Unit Operation 1.3. Unit Operation 1.3: Isolation of AP25047 HCI While stirring, the cool reaction mixture is quenched by addition of hydrogen chloride gas. A precipitate forms, and residual hydrogen chloride is removed from the suspension by a nitrogen purge. Tetrahydrofuran (THF) is replaced with toluene by an azeotropic distillation under reduced pressure. The resulting warm slurry is filtered in an agitated filter dryer and the filter cake is triturated and washed with warm toluene. The content of process impurity AP291 16 is determined by IPC-4 (HPLC). If the IPC-4 criterion is met, the wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 35 – 45C (jacket temperature). The drying is monitored by IPC-5 (LOD, gravimetric). If the IPC-5 criterion is met, the crude AP25047 HCI is discharged and packaged in FEP bags in a plastic container. The isolated AP25047 HCI can be held for up to 7 days prior to forward processing. Unit Operation 1.4: Work-up The crude AP25047 HCI solid is charged to a reactor with dichloromethane (DCM) and washed with aqueous ammonia. The aqueous phase is back extracted with DCM for yield recovery purposes and the combined organic phase is washed a second time with aqueous ammonia. The organic layer is then washed with aqueous hydrochloric acid until the aqueous phase reaches a pH of 1-2, as indicated by IPC-6 (pH strips). If the IPC-6 criterion is met, the organic phase is treated with aqueous sodium bicarbonate until the aqueous wash reaches a pH of NLT 7, as indicated by IPC-7 (pH strips). The organic phase is briefly concentrated followed by the addition of fresh dichloromethane. The organic solution is passed through a silica gel pad, which is then rinsed with additional fresh dichloromethane for increased product recovery. Unit Operation 1.5: Crystallization of AP25047 The dichloromethane solution is concentrated under reduced pressure, and the dichloromethane is replaced with 2-propanol by azeotropic distillation under reduced pressure to the targeted final volume range. The resulting suspension is then cooled and further aged with agitation. Unit Operation 1.6: Isolation / Drying The precipitated product is isolated in an agitated filter dryer under a flow of nitrogen, and the filter cake is rinsed with 2-propanol. The wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 45 – 55C (jacket temperature). The drying is monitored by IPC-8 (LOD, gravimetric). If the IPC-8 criterion is met, the product is sampled and packaged into polyethylene bags and placed within a heat sealed mylar coated aluminum foil bag, within an HDPE shipping container (Expected yield range, 65 – 89%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromoimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; MURRAY, Christopher, K.; ROZAMUS, Leonard, W.; CHABER, John, J.; SHARMA, Pradeep; WO2014/93579; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 18087-73-5, A common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 28; N-[ (1R,6S)-6-Amino-2,2-difluorocyclohexyl]-5-chloro-4-(imidazo[1,2-b]pyridazin-3-yl)-1,3- thiazole-2-carboxamide; Step 1. 1 -(Imidazo[1,2-b]pyridazin-3-yl)ethanone; 3-Bromoimidazo[1,2-b]pyridazine (1.0 g, 5.05 mmol), tributyl(l-ethoxyvinyl)tin (3.41 mL, 10.1 mmol), and PdCb(PPh3)2 (354 mg, 0.505 mmol), were added to a sealed tube. DMF (25.2 mL) was added and the reaction purged with nitrogen for 5 minutes. The reaction was heated at 100 C for 18 h. The reaction was cooled to room temperature and quenched with aqueous saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (x 3) and the combined organic layers were dried with magnesium sulfate, Filtered, and concentrated under reduced pressure. The residue was diluted with methanol (10 mL) and HCl in 1,4-dioxane (1.26 mL, 5.05 mmol, 4M) was added. The solution was stirred at room temperature for 1 h. The reaction was then quenched with aqueous saturated sodium bicarbonate and extracted with ethyl acetate (x 3). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) delta 8.76 (d, 1H); 8.55 (s, 1H); 8.31 (d, 1H); 8.49 (dd, 1H); 2.64 (s, 3H). LRMS (APCI) calc’d for (C8H7N3O) [M+H]+, 162.1; found 162.1.

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; ALTMAN, Michael, D.; BILODEAU, Mark, T.; LIM, Jongwon; NORTHRUP, Alan; STANTON, Matthew, G.; TAOKA, Brandon, M.; WO2010/83145; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 18087-73-5, These common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Tetrakis(triphenylphosphine)palladium(0) (64 mg, 55 pmol) and sodium carbonate (118 mg, 1.11 mmol) were added to a solution of 3-bromoimidazo[1,2-b]pyridazine (110 mg, 0.555 mmol) and C7 (295 mg, 0.610 mmol) in 1,4-dioxane (5 mL) and water (1 mL). The reaction mixture was degassed and purged with nitrogen several times, then placed in a sealed tube and heated at 120 C in a microwave reactor for 30 minutes. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 30 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL), dried over sodium sulfate, filtered, and concentratedin vacuo. Preparative thin layer chromatography (Eluent: ethyl acetate) provided the product as a yellow solid. Yield: 120 mg, 253 mmol, 46%. LCMS m/z 475.1 [M+H].

Statistics shows that 3-Bromoimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 18087-73-5.

Reference:
Patent; PFIZER INC.; GALATSIS, Paul; HAYWARD, Matthew Merrill; KORMOS, Bethany Lyn; WAGER, Travis T.; ZHANG, Lei; HENDERSON, Jaclyn Louise; KURUMBAIL, Ravi G.; VERHOEST, Patrick Robert; STEPAN, Antonia Friederike; WO2015/92592; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary