Category: 51376-06-8

Related Products of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

6-(Methylsulfonyl)-4-quinolinamine (50 mg, 0.225 mmol), 5-bromo-2,1,3-benzoxadiazole, Pd2dba3 (20.60 mg, 0.022 mmol), BINAP (14.01 mg, 0.022 mmol), and sodium tert-butoxide (43.2 mg, 0.450 mmol) were added to a vial which was purged with nitrogen. Toluene (2250 mul) was then added and the reactions were heated to 120 C for 20 min via microwave. It was then concentrated, redissolved in DMSO, filtered, and purified by RP HPLC to afford the title compound as a solid (11 mg, 14 %). 1H NMR (400 MHz, DMSO-d6) delta 9.26 (s, 1H), 8.82 (d, J = 5.1 Hz, 1H), 8.39 (d, J = 8.5 Hz, 1H), 8.23 (m, 2H), 7.95 (br. s, 1H), 7.72 (d, J = 9.5 Hz, 1H), 7.40 – 7.46 (m, 1H), 3.38 (s, 3H); MS (m/z) 341.1 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[c][1,2,5]oxadiazole, its application will become more common.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; HAILE, Pamela, A.; HARRIS, Philip, Anthony; LAKDAWALA SHAH, Ami; KING, Bryan, W.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SEHON, Clark, A.; EIDAM, Patric; EP2566477; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 51376-06-8, 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. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

l-(2-((2S,4R)-4-Fluoro-2-((2-fluoro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)carbamoyl)pyrrolidin-l-yl)-2-oxoethyl)-lH-indazole-3-carboxamide, 5- bromobenzo[c][l,2,5]oxadiazole, Pd(dppf)Cl2 and potassium carbonate were taken up in a pressure tube under argon. To this mixture, 8 mL of dioxane and 2 mL of water were added. The mixture was bubbled with argon for 5 min and the vial was stoppered and subjected to microwave irradiation at 100 C for 45 min. The volatiles were removed under reduced pressure and the residue was purified by ISCO (0-5 % MeOH in CH2CI2) to afford compound 68. 1HNMR (400 MHz, DMSO) (major rotamer) delta 2.10 – 2.20 (m, 1H), 2.57-2.63 (m, 1H), 3.89 – 4.04 (m, 1H), 4.24 (dd, J = 12.7, 21.8 Hz, 1H), 4.78 (t, J = 8.3 Hz, 1H), 5.47 (d, J= 17.2 Hz, 1H), 5.55 (d, J = 52.4 Hz, 1H), 5.67 (d, j = 17.2 Hz, 1H), 7.23-7.31 (m, 2H), 7.36 (s, 1H), 7.39 – 7.46 (m, 2H), 7.59 – 7.64 (m, 2H), 7.74 (d, J= 9.3 Hz, 1H), 7.98 (t, J= 7.8 Hz, 1H), 8.11 – 8.25 (m, 3H), 10.05 (s, 1H). 19F- MR (DMSO-de ) (major rotamer): delta -128.8, -175.9.

The synthetic route of 5-Bromobenzo[c][1,2,5]oxadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, 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. SDS of cas: 51376-06-8

General procedure: Methyl 5-boronofuran-2-carboxylate (8, 1.3mmol), the appropriate bromo derivatives (10, or 12, or 13, 1.0mmol) and bis(triphenylphosphine)palladium (II) dichloride (5% mol) were dissolved in dry 1,4-dioxane (10mL), under nitrogen atmosphere. A 2M sodium carbonate solution (2mmol) was then added and the resulting mixture was stirred in a microwave synthesizer (Biotage Initiator Classic) for 1hat 60C. After completion, the solution was cooled to room temperature and then filtered on a celite pad. The filtrate was diluted with water and extracted with ethyl acetate (3×4mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo.

The synthetic route of 5-Bromobenzo[c][1,2,5]oxadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chiarelli, Laurent R.; Mori, Matteo; Barlocco, Daniela; Beretta, Giangiacomo; Gelain, Arianna; Pini, Elena; Porcino, Marianna; Mori, Giorgia; Stelitano, Giovanni; Costantino, Luca; Lapillo, Margherita; Bonanni, Davide; Poli, Giulio; Tuccinardi, Tiziano; Villa, Stefania; Meneghetti, Fiorella; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 754 – 763;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

[00779] Intermediate 85: 2,1 ,3-benzoxadiazol-5-amine[00780] In a dry, nitrogen purged 5-10 mL microwave tube were successivelly introduced 5-bromo-2,1 ,3-Benzoxadiazole (200mg, 1.01 mmol), Pd2(dba)3 (46mg, 0.OSmmol) and tri-tertbutylphosphonium tetrafluoroborate (58mg, 0.2Ommol) and toluene (1 mL). The tube was evacuated/backfilled with nitrogen and then sealed. Lithium bis(trimethylsilyl)amide (1.0 M in toluene, 2mL, 2mmol) was added and the reaction mixture was thermally heated at 50 C overnight. After cooling to room temperature, the reaction mixture was diluted with ether (2OmL) and thesilylamide was deprotected by adding 2-3 drops of 1 M HCI(aq). The mixture was transferred to a separatory funnel and washed with sat. aq. NaHCO3 (lOmL). The organic layer was dried over Na2504, filtered and concentrated in vacuo. The residue was purified via column chromatography using an eluent of 0-100% EtOAc in heptane. Three main fractions were collected containing the expected product and unprotected I partially deprotecetd silyl amide. The fractions were pooled,concentrated in vacuo and the residue dissolved in THF (1 mL). 1 M HCI(aq) (1 mL) was added and the mixture was stirred at room temperature for 1 hour. The mixture was made alkaline with 1 M NaOH(aq) and extracted with EtOAc (3 x 1 OmL). The combined organic layers were washed with brine (l0mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified via column chromatography using an eluent of 0-100% EtOAc in heptane to give 2,1 ,3-benzoxadiazol-5-amine (57mg, 0.42mmol, 42%) as a yellow-green solid.1H NMR (DMSO-d6, 400MHz) O/ppm: 7.76 (1H, dd, J= 9.5Hz, 0.6Hz), 7.14 (1H, dd, J= 9.5Hz,1.8Hz), 6.43 (2H, brs), 6.35 (1H, dd, J= 1.8Hz, 0.6Hz).MS Method 2: RT: 1.22 mi mlz 136.0 [M+H]

The synthetic route of 51376-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

5-bromo-2,1,3-benzoxadiazole (0.17 g) (which can be prepared according to Org. Proc. Res. Dev., (2003), 7, 436-445 at page 437), triethylamine (0.11 g) and dichlorobistriphenyl-phosphine palladium (II) (0.12 g) were added to a solution of N- ({(5S)-3-[3-fluoro-4-(trimethylstannyl)phenyl]-2-oxo-1,3-oxazolidin-5- yl}methyl)acetamide (0.18 g) (which can be prepared according to Example 8 of WO 01/94342, page 52) in dry dimethyl formamide (15 mL) and the reaction mixture was heated at 100 C for about 3 hours, cooled and diluted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography using 2 % methanol in dichloromethane as eluent to yield the title compound (0.14 g). Melting point: 156-165 C; EMS (m/z): 388 (M+H); 1HNMR(CDCB): delta 7.91 (m, 2H), 7.62 (m, 2H), 7.52 (t, 1H), 7.35 (dd, 1H), 6.10 (t, 1H), 4.84 (m, 1H), 4.12 (t, 1H), 3.87 (t, 1H), 3.71 (m,2H), 2.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[c][1,2,5]oxadiazole, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 51376-06-8

5-bromo-2,1,3-benzoxadiazol (2.74 g) (which can be prepared according to Org. Proc. Res. Dev., (2003), 7, 436-445), cesium carbonate (5.38 g), 2,2′- bis(diphenylphosphino)-1,1′-binapthyl (0.68 g) and tris-(dibenzylideneacetone) dipalladium(O) (0.5 g) were added to a solution of (5S)-3-[3-fluoro-4-(piperidin-4- yloxy)phenyl]-5-[(isoxazol-3-ylamino)methyl]-1,3-oxazolidin-2-one (5 g) (obtained from Step b) in dry dimethylformamide (15 mL) and the reaction mixture was heated at 100 C for about 17 hours. The reaction mixture was filtered and the solvent was evaporated. The crude product thus obtained was purified by column chromatography using 1 % methanol in dichloromethane to yield the title product (0.4g). Melting point: 134-140 C; EIMS (m/z): 495.25;1HNMR(DMSO): delta 8.41 (s, 1H), 7.88 (d, 1H), (d, 1H), 7.6 (dd, 1H), 7.32 (t, 1H), 7.25 (d, 1H), 6.88 (s, 1H), 6.56 (t, 1H), 6.03 (s, 1H), 4.8 (m, 1H), 4.63-4.62 (m, 1H), 4.17 (t, 1H), 3.81 (m, 4H), 3.49-3.43 (m, 3H), 2.07 (m, 2H), 1.8 (m, 2H).

The synthetic route of 51376-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 51376-06-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 51376-06-8 name is 5-Bromobenzo[c][1,2,5]oxadiazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Cesium carbonate (0.46 g), 5-bromo-2,1,3-benzoxadiazole (0.23 g), 2,2′- bis(diphenylphosphino)-1,1′-binapthyl (0.074 g) and tris-(dibenzylideneacetone) dipalladium(O) (0.054 g) were added to a solution of N-{[(5S)-3-(3-fluoro-4-piperazin-1- ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (0.4 g) (which can be prepared according to Example l(k) in WO 93/23384, at page 14) in dry dimethyl formamide (15 mL) and the reaction mixture was heated at 100 C for 17 hours. The reaction mixture was filtered and the solvent was evaporated. The crude product thus obtained was purified by column chromatography using 2 % methanol in dichloromethane and sonicated in ether to yield the title compound (0.12 g).Melting point: 201-222 C; EIMS (m/z): 455;1HNMR(CDCl3): delta 7.71 (d, 1H), 7.48 (dd, 1H), 7.33 (dd, 1H), 7.12 (dd, 1H), 6.98 (t, 1H), 6.79 (s, 1H), 5.99 (t, 1H), 4.76 (m, 1H), 4.02 (t, 1H), 3.85-3.55 (m, 3H), 3.47 (m, 4H), 3.24 (m, 4H), 2.03 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromobenzo[c][1,2,5]oxadiazole, and friends who are interested can also refer to it.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 51376-06-8, 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 51376-06-8 as follows.

Triethylamine (0.12 g), 5-bromo-2,1,3-benzoxadiazole (0.19 g) and dichlorobistriphenylphosphine palladium(II) (0.13 g) were added to a solution of N-({(5S)- 3 – [3 , 5 -difluoro-4-(trimethylstannyl)phenyl] -2-oxo- 1 ,3 -oxazolidin-5 -yl } methyl)acetamide (0.21 g) (which can be prepared according to Example 8 of WO 01/94342, at page 52) in dry dimethyl formamide (15 mL) and the reaction mixture was heated at 100 C for about 3 hours. The reaction mixture was filtered and diluted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated. The crude EPO product was purified by column chromatography using 2 % methanol in dichloromethane as eluent to yield the title compound (0.035 g).Melting point: 165-168 C; EMS (m/z): 388;1HNMR(CDC13): delta 7.92 (m, 2H), 7.48 (dd, 1H), 7.32 (dd, 2H), 5.98 (t, 1H), 4.85 (m, 1H), 4.09 (t, 1H), 3.84 (m, 1H), 3.72 (m, 2H), 2.03 (s, 3H).

According to the analysis of related databases, 51376-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, 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 51376-06-8, Quality Control of 5-Bromobenzo[c][1,2,5]oxadiazole

5-Bromo-2,1,3-benzoxadiazole (10 g, 50.3 mmol) was dissolved in toluene (300 ml) and added Lithium chloride (6.4 g, 150 mmol), Pd(Ph3P)4 (2.90 g, 2.50 mmol), and allyl tributyltin (19 ml, 60 mmol). The reaction mixture was degassed and refluxed under N2 for 3 hrs. It was cooled and poured into water then extracted with ethyl acetate. The organic layer was washed with brine 1x, dried and evaporated to dryness. The residue was chromatographed through 120g ISCO Redi-Sep columns and eluted with 0-10% ethyl acetate / hexane to yield 5-allyl-2,1,3-benzoxadiazole. 1H-NMR (500 MHz, DMSO): delta ppm 7.96 (d, J=9.1 Hz, 1H), 7.44(d, J= 9.1 Hz, 2H), 5.95-6.04 (m, 1H), 5.17 (d, J=14.7Hz, 1H), 5.15 (d, J=8.9Hz, 1H), 3.50 (d, J= 6.7Hz, 2H)

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, 5-Bromobenzo[c][1,2,5]oxadiazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; TANG, Haifeng; PASTERNAK, Alexander; YANG, Lihu; WALSH, Shawn, P.; PIO, Barbara; SHAHRIPOUR, Aurash; TEUMELSAN, Nardos; (111 pag.)EP2632465; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, 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 51376-06-8, Computed Properties of C6H3BrN2O

5-bromo-2,1,3-benzoxadiazole (0.71 g), cesium carbonate (1.4 g), 2,2′- bis(diphenylphosphino)-1,r-binapthyl (0.17 g) and Tris-(dibenzylideneacetone) dipalladium(O) (0.13g) were added to a solution of (5S)-3-[3-fluoro-4-(piperidin-4- yloxy)phenyl]-5-[(isoxazol-3-ylamino)methyl]-1,3-oxazolidin-2-one (1.3 g) (obtained from Step b) in dry dimethylformamide (15 mL) and the reaction mixture was heated at 100 C for about 17 hours. The reaction mixture was filtered and the solvent was evaporated. The crude product thus obtained was purified by column chromatography using 1 % methanol in dichloromethane to yield the title product (0.07g).Melting point: 75-100 C; EIMS (m/z): 534.21; 1HNMR(DMSO): delta 8.16 (s, 1H), 7.66 (d, 1H), 7.48 (dd, 1H), 7.3 (m, 2H), 7.17 (d, 1H), 7.08-7.05 (t, 1H), 6.75 (s, 1H), 4.99 (m, 1H), 4.53 (m, 3H), 4.14-4.11 (t, 1H), 3.95 (t, 1H), 3.61 (m, 2H), 3.3 (m, 2H), 2.04 (m, 4H).

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, 5-Bromobenzo[c][1,2,5]oxadiazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary