Month: June 2021

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Safety of 5-(Bromomethyl)benzo[d][1,3]dioxole

General procedure: A 10-mL round-bottom flask was equipped with a magnetic stir bar and a reflux condenser. Then 0.4 mmol of alkyl halide and 0.44 mmol of sodium azide were added to 1.5 mL of anhydrous dimethylformamide. The reaction mixture was stirred at 60 C for 2 h under nitrogen atmosphere. After cooling to room temperature, TLC indicated the disappearance of the starting material. 0.44 mmol of active ketone and 0.44 mmol of DBU were then added to the reaction mixture, which was stirred for 3 h at 60 C. Brine (40 mL) was added to the reaction mixture and washed with EtOAc (3 10 mL). The organic layer was dried (Na2SO4) and the solvent evaporated under reduced pressure. Flash column chromatography afforded the pure triazole.

The synthetic route of 2606-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gonzalez-Calderon, Davir; Aguirre-De Paz, Jose G.; Gonzalez-Gonzalez, Carlos A.; Fuentes-Benites, Aydee; Gonzalez-Romero, Carlos; Tetrahedron Letters; vol. 56; 13; (2015); p. 1713 – 1715;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 53078-85-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 53078-85-6 as follows.

5-methyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (2): A solution of 2-bromo-5-methylani fine (1.5 g, 8.0 mmol) in dimethyl sulfoxide (20.0 mL) was treated with bis-pinacolatodiborane(2.4 g, 9.7mmol), potassium acetate (2.4 g, 24 mmol), and [1,1 ‘Bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with dichloromethane (329 mg, 0.04 mmol) at 110 C for 6 h. After completion of the reaction, the reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to afford 2 (320 mg, 17%) as a pale yellow liquid. 1H NMR (400 MHz, DMSO-d6): delta 1.26 (s, 12H), 2.13 (s, 3H), 5.37 (s, 2H), 6.29 (d, J = 7.5 Hz, 1H), 6.37 (s, 1H), 7.23 (d, J = 7.5 Hz, 1H). MS m/z (M+H): 234.2

According to the analysis of related databases, 53078-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2789-89-1,Some common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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.

General procedure: A glass tube equipped with a magnetic stir bar was charged with isoxazole 1 (0.2 mmol), alkyne 2 (0.62 mmol, 3.1 equiv),[Cp*Rh(MeCN)3](SbF6)2 (0.008 mmol, 4.0 mol%), and Cu(OAc)2 (0.8mmol, 4.0 equiv). The tube was evacuated and backfilled with N2 (3 ×)followed by addition of 1,4-dioxane (4.0 mL) via syringe. The resulting mixture was heated at 100 C for 12 h. After cooling to r.t., the mixture was poured into water and extracted with EtOAc (3 ×). The combined organic extracts were washed with brine, dried (Na2SO4), andc oncentrated under reduced pressure. The residue was subjected to column chromatography (silica gel) to afford the corresponding product .Further purification was performed by GPC if required. Note: the coupling products 3 exhibit broadened and split peaks inNMR spectra owing to the presence of rotamers, and the following data are reported as appeared in the spectra.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(4-bromophenyl)ethyne, its application will become more common.

Reference:
Article; Noguchi, Teppei; Nishii, Yuji; Miura, Masahiro; Synthesis; vol. 51; 1; (2019); p. 258 – 270;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 327-51-5,Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

(a) 4-bromo-2,5-difluorobenzoic acid To a 780C solution of 1,4-dibromo-2,5-difluorobenzene (2.72 g, 9.99 mmol) in dry Et20 (30 mL) under an inert atmosphere was added 2.5 M n-butyllithium solution in hexanes (4 mL, 9.99 mmol) drop-wise and the mixture left stirring for 2 h. Crushed CO2 pellets were added slowly and the mixture was allowed to warm to ambient temperature and left stirring for 1 h. After quenching with 1M aqueous HCI (10 mL) the mixture was basified with 1M aqueous NaOH (70 mL) and then washed with Et20 (2 x 50 mL). The aqueous layer was acidified with 1M aqueous HCI (80 mL) and extracted with Et20 (3 x 100 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and solvent was removed in vacuo to give 4-bromo-2,5-difluoro benzoic acid (2.3 g, 97 %) as an off-white solid, which was used without further purification.1H NMR (Method B) (CDCI3): O ppm 9.50 (brs, 1H), 7.78 (dd, J= 8.2, 6.1 Hz, 1H), 7.46 (dd, J= 9.3, 5.4 Hz, 1H); LC-MS (Method C) 234.9/236.9 [M-H] RT 3.43 mm

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; RATCLIFFE, Andrew; HUXLEY, Anthony; LYTH, David; NOONAN, Gary; KIRK, Ralph; UOSIS-MARTIN, Mario; STOKES, Neil; WO2015/155549; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 6911-87-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6911-87-1 as follows.

General procedure: Sulfonyl chloride derivative 1 or 2 (3.99mmol) was added gradually to a mixture of substituted amine (4.39mmol) and pyridine (2mL) in EtOAc with stirring at 0C. The reaction mixture was stirred at room temperature until the TLC indicated complete conversion of the sulfonyl chloride to the sulfonamide intermediate. The reaction mixture was dissolved in DCM and extracted (2×) with 10% NaOH. After the aqueous layer was acidified with 2N HCl, the precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the desired products (5-22, 173, 174), which were carried forward without further purification.

According to the analysis of related databases, 6911-87-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khanfar, Mohammad A.; Quinti, Luisa; Wang, Hua; Choi, Soo Hyuk; Kazantsev, Aleksey G.; Silverman, Richard B.; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 414 – 426;,
Bromide – Wikipedia,
bromide – Wiktionary

7051-34-5, name is (Bromomethyl)cyclopropane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 7051-34-5

Step 1: Synthesis of 4-(benzyloxy)-3-(cyclopropylmethoxy)benzaldehyde (119) 4-(benzyloxy)-3-hydroxybenzaldehyde (640 mg, 2.8 mmol) was dissolved in DMF (5 ml), then K2CO3 (774 mg, 5.6 mmol) and (bromomethyl)cyclopropane (544 mul, 5.6 mmol) were added, and the mixture was stirred at 90 C. for 2 hours. The reaction was diluted with Et2O and the organic phase was washed with NaHCO3 sat sol, water and brine, dried over Na2SO4 and evaporated under vacuum to give 750 mg of the desired product (yield 95%).

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Esposito, Oriana; Carzaniga, Laura; Capaldi, Carmelida; US2014/155391; (2014); A1;,
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

Electric Literature of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 4: 7-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-1-en-1-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine A mixture of tert-butyl(dimethyl) {[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]oxy}silane (450 mg, 1.33 mmol), 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (283 mg, 1.33 mmol), sodium carbonate (470 mg, 4.4 mmol), and [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II) (101 mg, 0.133 mmol) in tert-butyl alcohol (4.0 mL) and water (1.5 mL) was degassed with nitrogen, then stirred and heated at 110 C. for 2 h, then 95 C. overnight. The mixture was diluted with ethyl acetate, washed with saturated NaHCO3, water, dried over Na2SO4, filtered and concentrated. The product was purified by Biotage silica gel chromatography (0 to 50% EtOAc in hexanes) to give the desired product as off-white powders (242.3 mg, 53%). LCMS calcd for C18H29N4OSi (M+H)+: m/z=345.2. Found: 345.2.

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, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Wang, Xiaozhao; Barbosa, Joseph; Burns, David M.; Feng, Hao; Glenn, Joseph; He, Chunhong; Huang, Taisheng; Mei, Song; Zhuo, Jincong; (169 pag.)US2017/275290; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1073-39-8, 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (1 17 mg, 0.64 mmol) in THF (2 ml) was added dropwise n-BuLi (2.5 M in n-hexane) (0.25 ml, 0.64 mmol) at -78 C under N2. The reaction mixture was stirred at -78C for 30 min. 4-(benzyloxy)-2-methyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6- (benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzaldehyde ((240 mg, 0.32 mmol) in THF (1 ml) was added dropwise at -78C. The reaction mixture was stirred at -78C for 1 h. Saturated NH4CI (aq) was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :3 EA/PE) to (4-(benzyloxy)-2- methyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)- tetrahydro-2H-pyran-2-yl)phenyl)(1,2-dihydrocyclo-butabenzen-4-yl)methanol as a yellow oil. MS (ES) m/z: 875.5 [M+Na]+.

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, 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.

Acetic anhydride (2.27 eqiv) was added to a cooled 0 C solution of bromomethylaniline (1.00 eqiv) in chloroform (1.5 mL/mol) while maintaining the temperature below 40 C. The reaction mixture was allowed to warm to room temperature and was maintained for 1 h. Potassium acetate (0.29 eq) and isoamyl nitrite (2.15 eqiv) was added and the reaction mixture was heated at reflux for 18 h. The volatiles were removed under reduced pressure. Water (0.65 L/mol) was added to the residue and the mixture was concentrated. Concentrated hydrochloric acid (1 L/mol) was added to the residue and the mixture was heated at 50 C for 2 h. The mixture was allowed to cool to room temperature and the pH was adjusted to 10 by the slow addition of a 50% aqueous sodium hydroxide solution. The mixture was diluted with water (0.65 L/mol) and was extracted with ethyl acetate (2 x 1.2 L/mol). The combined extracts were washed with brine (1 L/mol) and dried over anhydrous sodium sulfate. The organic solution was filtered through a plug of silica gel (ethyl acetate wash), concentrated, and the residue was triturated with heptane (1 L/mol). The solids were collected by filtration, rinsed with heptane, and dried in a vacuum oven.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Memory Pharmaceuticals Corporation; WO2004/29050; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary