Category: 4887-88-1

Application of 4887-88-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a 0 C solution of 5-bromo-lH-benzimidazole (10.2 mmol) in dichloromethane (30 mL) was dropwise added bis( 1,1 -dimethylethyl) dicarbonate (1 1.2 mmol) and triethylamine (15.2 mmol). The reaction mixture was then stirred at room temperature overnight. The mixture was washed with water (3 x 10 mL) and brine, then dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude product.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; CHAUDHARI, Amita, M.; HALLMAN, Jason; LAUDEMAN, Christopher, P.; MUSSO, David, Lee; PARRISH, Cynthia, A.; WO2011/66211; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-88-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Prepared above 5-bromo -1H- benzo [d] imidazole (3.25g, 22.1mmol) in solution in THF (65 mL) of, Boc2O (5.79g, 26.5mmol), Et3N (3.35,33.15mmol) and DMAP (270mg, 2.21mmol) was added. The mixture was stirred for 4 hours at room temperature, then diluted with water (200mL), and extracted with ethyl acetate (200mL). The organic layer was washed with water (2 ¡Á 100 mL) and brine (100 mL), dried over Na2SO4, and concentrated to give 0601-187 as an oil (4.8g, 98%).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4887-88-1, The chemical industry reduces the impact on the environment during synthesis 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

5-Bromo-1H-benzo[d]imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% yield).

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-Bromo-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mortensen, Deborah S.; Perrin-Ninkovic, Sophie M.; Harris, Roy; Lee, Branden G.S.; Shevlin, Graziella; Hickman, Matt; Khambatta, Gody; Bisonette, Rene R.; Fultz, Kimberly E.; Sankar, Sabita; Bioorganic and Medicinal Chemistry Letters; vol. 21; 22; (2011); p. 6793 – 6799;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4887-88-1, A common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, molecular formula is C7H5BrN2, 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.

To a solution of crude, impure 5-bromobenzimidazole (46.2 g) and methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate (Synthesis, 1984, 10, 847-850) (42 g, 220 mmol) in 800 mL of CHCl3 was added N-methylimidazole (28 mL, 345 mmol). After 16 h, N-methylimidazole (17 mL, 220 mmol) and tert-butylchlorodimethylsilane (36 g, 240 mmol) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto celite. The crude mixture was purified by flash column chromatography (0-25% EtOAc:hexanes) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 3 eluting first and 29.2 g of Intermediate 4 eluting second (58%). (Intermediate 3, 5-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.77 (s, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.56 (dd, J=8.8 and 1.6 Hz, 1H), 7.25 (s, 1H), 3.76 (s, 3H), 0.99 (s, 9H), 0.27 (s, 6H). (Intermediate 4, 6-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.71 (s, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8 and 2.0 Hz, 1H), 7.26 (s, 1H), 3.77 (s, 3H), 0.99 (s, 9H), 0.26 (s, 6H).

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuntz, Kevin Wayne; Emerson, Holly Kathleen; Cheung, Mui; Badiang, Jennifer Gabriel; US2009/326029; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, 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. Quality Control of 5-Bromo-1H-benzo[d]imidazole

General procedure: N-(Azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamide TFA salt: 3-Amino-azetidine-1-carboxylic acid tert-butyl ester (1.2 g, 6.97 mmol) and (3-trifluoromethyl-benzoylamino)-acetic acid (1.57 g, 6.36 mmol) were treated with EDCI (1.57 g, 6.36 mmol), HOBT (1.22 g, 6.36 mmol) in DCM (10 mL) at room temperature for 4 hours. The reaction solution was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give yellow oil, which was then purified by silica gel column on a CombiFlash system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford 3-[2-(3-trifluoro-methyl-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butyl ester as white solid, 2.23 g, 80% yield. 1H NMR (400 MHz, CDCl3) d 8.10 (s, 1H), 8.02 (d, J = 6.6 Hz, 1H), 7.80 (d, J = 6.8 Hz, 1H), 7.56 (t, J = 6.5 Hz, 1H), 4.61 (m, 1H), 4.25 (t, J = 7.2 Hz, 2H), 4.18 (d, J = 5.5 Hz, 2H), 3.82 (t, J = 7.5 Hz, 2H), 1.41 (s, 9H). 3-[2-(3-Trifluoromethyl-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butyl ester (2.10 g, 5.24 mmol) was dissolved in 1:1 TFA and DCM mixed solution (10 mL) at room temperature. The reaction was stirred for another 2 hours. The solvent was removed and the residue was dried to give N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamide as a TFA salt containing extra TFA (colorless oil), ~ 2.5 g, 100% yield. 1H NMR (400 MHz, CDCl3) d 8.10 (s, 1H), 8.05 (d, J = 6.0 Hz, 1H), 7.78 (d, J = 6.2 Hz, 1H), 7.55 (m, 2H), 4.78 (m, 1H), 4.15 (d, J = 3.2 Hz, 2H), 3.95 (t, J = 7.0 Hz, 2H), 3.52 (t, J = 7.0 Hz, 2H).8-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene (PCT Int. Appl. WO2006064189, 0.292 g, 1.10 mmol), 5-bromobenzo[d][1,3]dioxole (Aldrich, 161 mg, 0.801 mmol), and tetrakis (triphenylphosphino)palladium(0) (Aldrich, 0.048 g, 0.042 mmol) were dissolved in 1,4-dioxane (9 mL), treated with 2M aqueous Na2CO3 (2.0 mL, 4.0 mmol), bubbled with argon for a few minutes, and heated to 100oC under reflux condenser for 24 h. After cooling to ambient temperature, the reaction was diluted with water (30 mL), extracted thrice with dichloromethane, aqueous layer acidified to ca. pH 7, extracted twice more with dichloromethane, and the combined organic layers washed with brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo to give an orange oil. This was purified by thin layer chromatography on silica gel (EtOAc) to give 5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzo[d][1,3]dioxole as a yellow solid (110 mg, 53%). 5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzo[d][1,3]dioxole (110 mg, 0.42 mmol) in MeOH (5 mL) was placed in a hydrogenation Par Shaker under 40 psi at room temperature using 5% Pd/C (~ 50 mg) as catalyst for 2 hour. The resulting solution was filtered through a pad of Celite , concentrated and purified by silica gel column on a CombiFlash system to afford 5-(1,4-dioxaspiro[4.5]decan-8-yl)benzo[d][1,3]dioxole as white solid, 91 mg, 82% yield. 5-(1,4-dioxaspiro[4.5]decan-8-yl)benzo[d][1,3]dioxole (91 mg, 0.35 mmol) was treated with 1N HCl ( ~ 2 mL) in acetone (4 mL) at room temperature for 4 hours. The reaction was neutralized with saturate NaHCO3 solution and the solvent was removed. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give yellow solid, which was then purified by silica gel column on a CombiFlash system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford 4-(benzo[d][1,3]dioxol-5-yl)cyclohexanone as white solid, 75 mg, 98% yield.4-(benzo[d][1,3]dioxol-5-yl)cyclohexanone (75 mg, 0.35 mmol) and N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamide TFA salt (151 mg, 0.50 mmol) in DCM (2 mL) was treated with TEA (0.1 mL, 0.75 mmol) for 10 min followed by NaBH(OAc)3 (Aldrich, 225 mg, 1.05 mmol) for another 4 hours at room temperature. The reaction was quenched with saturated sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted 3 times with chloroform and IPA “cocktail” (~ 3:1, v/v). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by a CombiFlash system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford two title compounds as white solids: 8a, less polar isomer (cis), 67 mg, 38% yield; 9a, more polar isomer (trans), 45 mg, 26% yield.

The synthetic route of 5-Bromo-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xuqing; Hufnagel, Heather; Markotan, Thomas; Lanter, James; Cai, Chaozhong; Hou, Cuifen; Singer, Monica; Opas, Evan; McKenney, Sandra; Crysler, Carl; Johnson, Dana; Sui, Zhihua; Bioorganic and Medicinal Chemistry Letters; vol. 21; 18; (2011); p. 5577 – 5582;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrN2

Step C-Methyl 5-(5-bromo-1H-henzimidazol-1-yl)-3-{[tert-butyl(dimethyl)silyl]oxy}thiophene-2-carboxylate and methyl 5-(6-bromo-1H-benzimidazol-1-yl)-3-{[tert-butyl(dimethyl)silyl]oxy}thiophene-2-carboxylate (Title Compounds)To a solution of crude, impure 5-bromobenzimidazole (48.2 g) and methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate (42 g, 220 mmol) in 800 mL of CHCl3 was added N-methylimidazole (28 ml, 350 mmol). After 16 h, N-methylimidazole (17 mL, 220 mmol) and tert-butylchlorodimethylsilane (36 g, 240 mmol) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto celite. The crude mixture was purified by flash column chromatography (0-25% EtOAc:bexanes) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 4 eluting first and 29.2 g of Intermediate 5 eluting second (58%). (Intermediate 4, 5-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.77 (s, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.58(dd, J=8.8 and 1.6 Hz, 1H), 7.25 (s, 1H), 3.78 (s, 3H), 0.99 (s, 9H), 0.27 (s, 6H). (Intermediate 5, 6-Br) 1H NMR (400 MHz, d6-DMSG) delta 8.71 (s, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8 and 2.0 Hz, 1H), 7.26 (s, 1H), 3.77(s, 3H), 0.99 (s, 9H), 0.28 (s, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4887-88-1.

Reference:
Patent; Kuntz, Kevin; Emmitte, Kyle Allen; Rheault, Tara Renae; Smith, Stephon; Hornberger, Keith; Dickson, Hamilton; Cheung, Mui; US2008/300247; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem