Category: 39513-26-3

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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1,3-dihydrobenzoimidazol-2-one

5-Bromo-1,3-dihydrobenzimidazol-2-one (1.30 g, 6.10 mmol), 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol Ester (1.77 g, 6.00 mmol), 1,1′-bisdiphenylphosphinoferrocene palladium dichloride (230 mg,0.314 mmol) and potassium carbonate (2.49 g, 18.0 mmol) were mixed in N,N-dimethylformamide (30 mL).The oxygen was replaced by nitrogen, and then heated to 100 C for 16 hours.The reaction system was diluted with ethyl acetate (300 mL), and the organic phase was washed with water (100 mL×2).The mixture was washed with saturated brine (100 mL × 5) and dried over anhydrous sodium sulfate.The desiccant was removed by filtration, and the solvent was concentrated under reduced pressure.Column chromatography purification (petroleum ether / ethyl acetate / ethanol = 12 / 3 / 1, 3 / 3 / 1),A pale yellow solid (300 mg, yield 17%) was obtained.

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 39513-26-3.

Reference:
Patent; Maidikang (Shanghai) Bio-pharmaceutical Technology Co., Ltd.; Dang Zhu; Ke Lisiting·juecai; Luo Zhen; Wang Liugang; Bao Dan; Qi Tafamingrenqingqiubugongkaixingming; (106 pag.)CN109956931; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39513-26-3, 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. 39513-26-3 name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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.

To a stirred solution of 5-bromo-lH-benzo[d]imidazol-2(3H)-one104 (930 mg) in a mixture of dioxane (47 ml) and 1 M aqueous sodium carbonate (24 ml) was added 5- quinolylboronic acid105 (906 mg). The reaction mixture was purged three times with Argon before adding 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.358 g) and palladium(II) acetate (0.098 g). The reaction mixture was refluxed for 4 hours. Dioxane was removed by evaporation and ethyl acetate was added. The solid obtained was filtered, dissolved in dichloromethane and washed with water. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, eluent: 0 to 5% of methanol in dichloromethane) to afford 5-(2-isopropyl-lH-imidazol-l-yl)-2- nitroaniline (85mg, 27%) as an orange solid. MS (ISP): 247.2 ([M+H]+). The organic layer off and the filter cake was washed with methanol. The filtrate was concentrated in vacuo to 5- quinolin-5-yl-l,3-dihydro-benzoimidazol-2-one as a dark brown solid (949 mg). MS (ISP): 262.2 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,3-dihydrobenzoimidazol-2-one, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39513-26-3, These common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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.

5-bromo-1,3-dihydro-2H-benzo[d]imidazol-2-one (50 mg, 0.235 mmol), 20 (124 mg, 0.352 mmol), and Pd(PPh3)4 (14mg, 5 mol%), were combined in a microwave vial and flushed with N2 for5 min. Dioxane (3 mL) and aq. K3PO4 (1 M, 0.5 mL) wereadded and the mixture was heated in a Biotage microwave at 100 C for 1 h. H2O(3 mL) and EtOAc (7 mL) were added and the organic layer was separated, driedusing Na2SO4 and evaporated. Gilson HPLC purificationafforded 22 (1.44 mg, 2%).

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lotesta, Stephen D.; Marcus, Andrew P.; Zheng, Yajun; Leftheris, Katerina; Noto, Paul B.; Meng, Shi; Kandpal, Geeta; Chen, Guozhou; Zhou, Jing; McKeever, Brian; Bukhtiyarov, Yuri; Zhao, Yi; Lala, Deepak S.; Singh, Suresh B.; McGeehan, Gerard M.; Bioorganic and Medicinal Chemistry; vol. 24; 6; (2016); p. 1384 – 1391;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39513-26-3,Some common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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 stirred solution of 5-bromo-1H-benzo[d]imidazol-2(3H)-one (1.0 g,4.69 mmol)inTHF (10 mL)at 0 oc was added NaH (469 mg,11.74 mmol,60%)and the mixture was stirred10 for 30 min. Methyliodide (0.88 mL,14.08 mmol)was added dropwise and the mixture stirred atroom temperature for an additional 16 h. The mixture was quenched with saturated NH4Cl (20mL)and extracted with EtOAc (20 mL x 2). The combined organic layers were dried overanhydrous Na2S04,filtered and concentrated in vacuo. The crude residue was purified by silicagel chromatography (petroleum ether I EtOAc = 5: 1)to give the title compound (630 mg,56%)15 as a white solid. 1HNMR (400 MHz,CDCl3)8 7.23 (d,J= 8.4 Hz,1H),7.12 (d,J= 2.0 Hz,1H),6.84 (d,J= 8.4 Hz,1H),3.41 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,3-dihydrobenzoimidazol-2-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, belongs to imidazoles-derivatives 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 39513-26-3, HPLC of Formula: C7H5BrN2O

Sodium hydride (60% in mineral oil, 256 mg, 6 4 mmol) was added to a solution of 5- Bromo-1 3-diotahydro-1 ,3-diotahydro-benzoiotarmdazol-2-one (427 mg, 2 mmol) in DMF (20 mL) at room temperature After 10 min, iodomethane (710 mg, 5 mmol) was added dropwise, and the resulting mixture was stirred at room temperature for overnight (15 hrs) The reaction was quenched with water (100 mL) and extracted with ethyl acetate (125 mL x 3) The combined extracts were washed with water (100 mL x2), saturated aqueous NaCI solution (100 mL), dried with MgSO4 After concentration, a pale yellow solid was obtained (539 mg) without further punfication

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-1,3-dihydrobenzoimidazol-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39513-26-3, A common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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 1095 Step 1 A solution of Compound 1095A in DMF (2 ml) was treated sequentially with sodium hydride (28 mg, 60% dispersion in oil, 0.70 mmol) and iodomethane (0.04 ml, 80 mg, 0.56 mmol). The reaction mixture was stirred overnight at rt. The reaction was quenched with water, diluted with EtOAc, and washed sequentially with water and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to give crude Compound 1095B (37 mg, 68%), which was used without further purification.

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Bromo-1,3-dihydrobenzoimidazol-2-one

General procedure: To a solution of 5-bromo-lH-benzo[d]imidazol-2(3H)-one80 (50 mg) in dioxane (1 ml) were added pyridin-3-ylboronic acid 81 (43.3 mg), [l,l-bis(diphenyl- phosphino)ferrocene]dichloropalladium(II) (17.2 mg) and 2 M aq. sodium carbonate solution (235 mu). The reaction mixture was heated at 100 C for 18 hours. The reaction mixture was then cooled to room temperature, diluted with water (50 ml), and extracted twice with ethyl acetate (2 x 30ml). The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel; 12 g; eluent: dichloromethane/methanol = 100/0 to 95/05 in 10 minutes) to afford 5-(pyridin-3-yl)-lH- benzo[d]imidazol-2(3H)-one (12 mg, 23%) as a red solid. MS (ISP): 212.1 ([M+H]+).

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrN2O

5-Bromo-1,3-dihydrobenzimidazol-2-one (1.30 g, 6.10 mmol), 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol Ester (1.77 g, 6.00 mmol), 1,1′-bisdiphenylphosphinoferrocene palladium dichloride (230 mg,0.314 mmol) and potassium carbonate (2.49 g, 18.0 mmol) were mixed in N,N-dimethylformamide (30 mL).The oxygen was replaced by nitrogen, and then heated to 100 C for 16 hours.The reaction system was diluted with ethyl acetate (300 mL), and the organic phase was washed with water (100 mL×2).The mixture was washed with saturated brine (100 mL × 5) and dried over anhydrous sodium sulfate.The desiccant was removed by filtration, and the solvent was concentrated under reduced pressure.Column chromatography purification (petroleum ether / ethyl acetate / ethanol = 12 / 3 / 1, 3 / 3 / 1),A pale yellow solid (300 mg, yield 17%) was obtained.

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 39513-26-3.

Reference:
Patent; Maidikang (Shanghai) Bio-pharmaceutical Technology Co., Ltd.; Dang Zhu; Ke Lisiting·juecai; Luo Zhen; Wang Liugang; Bao Dan; Qi Tafamingrenqingqiubugongkaixingming; (106 pag.)CN109956931; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39513-26-3,Some common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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 5-bromo-lH-benzo[d]imidazol-2(3H)-one80 (50 mg) in dioxane (1 ml) were added pyridin-3-ylboronic acid 81 (43.3 mg), [l,l-bis(diphenyl- phosphino)ferrocene]dichloropalladium(II) (17.2 mg) and 2 M aq. sodium carbonate solution (235 mu). The reaction mixture was heated at 100 C for 18 hours. The reaction mixture was then cooled to room temperature, diluted with water (50 ml), and extracted twice with ethyl acetate (2 x 30ml). The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel; 12 g; eluent: dichloromethane/methanol = 100/0 to 95/05 in 10 minutes) to afford 5-(pyridin-3-yl)-lH- benzo[d]imidazol-2(3H)-one (12 mg, 23%) as a red solid. MS (ISP): 212.1 ([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-Bromo-1,3-dihydrobenzoimidazol-2-one, its application will become more common.

Reference of 39513-26-3, These common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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.

Iodomethane (2.41 g) was added to a suspension of 5-bromo-1,3-dihydro-benzoimidazol-2-one (1.65 g) and potassium tert-butoxide (1.91 g) in DMA (20 ml). The mixture was stirred overnight at room temperature. The mixture was poured to 2.5N aqueous HCl (80 ml) and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated in vacuo. Heptane (50 ml) was added to the residue and the mixture was filtered. The residue was washed with diethyl ether and dried in vacuo to give the title compound (1.1 g) as a light brown solid. MS (m/e)=241.1 [M+H+].

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.