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CAS No. : | 913297-44-6 | MDL No. : | MFCD27932420 |
Formula : | C8H7BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RTGYXYYWJABYDE-UHFFFAOYSA-N |
M.W : | 227.06 | Pubchem ID : | 59635470 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 190℃; for 2h;microwave irradiation; | A suspension of 50 mg (0.220 mmol) of 7-bromo-l- methyl-1, 3-dihydro-2No.-benzimidazol-2-one, 0.035 mL (0.440 mmol) of 3-methylpyrazole, 42 mg (0.0220 mmol) of copper (I) iodide and 61 mg (0.440 mmol) of potassium carbonate in 1 mL of l-methyl-2-pyrrolidinone was stirred by microwave irradiation at 190 0C for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (Xl) , dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25% ethylacetate/n-hexane mixture to give 57 mg of a mixture containing the title EPO <DP n="125"/>compound.1H NMR (CDCl3) delta 2.34 (3H, s) , 2.98 (3H, s) , 6.26 (IH, d, J = 2.2 Hz), 6.97-7.18 (3H, m) , 7.57 (IH, d, J = 2.2 Hz), 9.60 (IH, br s) . MS Calcd. : 228; Found: 229 (M+H) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In toluene; at 100℃; for 4h; | mixture of 280 mg (1.23 mmol) of 7-bromo-l-methyl- l,3-dihydro-2No.-benzimidazol-2-one, 222 mg (1.48 mmol) of 2- ethylphenylboronic acid, 113 mg (0.0123 mmol) of tris (dibenzylideneacetone) dipalladium, 29 mg (0.0615 mmol) of X-Phos and 522 mg (2.46 mmol) of potassium phosphate in 9 mL of toluene was stirred at 100 0C for 4 hours. After cooling, the reaction mixture was diluted with water and ethyl acetate and passed through celite. The filtrate was extracted with ethyl acetate (X2) . The combined organic layer was washed with brine (Xl) , dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-65% ethylacetate/n-hexane gradient mixture to give 200 mg (64%) of the title compound. 1H NMR (CDCl3) delta 1.04 (3H, t, J = 7.7 Hz), 2.34-2.52 (2H, m) , 2.84 (3H, s) , 6.86-6.98 (2H, m) , 7.05-7.08 (2H, m) , EPO <DP n="120"/>7.18-7.39 (3H, m), 8.58 (IH, br s). MS Calcd. : 252; Found: 253 (M+H) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With trichlorophosphate; at 110℃; for 48h; | 7-Bromo-l-methyl-l, 3-dihydro-2H-benzimidazol-2-one (2.20 g, 9.69 mmol) was dissolved in phosphorous oxychloride (30 mL) and heated at 1100C for 2 days. The reaction mixture was allowed to cool to room temperature, poured into water with an ice and stirred for 1 h. The mixture was extracted with ethyl acetate, washed with aqueous sodium bicarbonate EPO <DP n="122"/>solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 50% ethyl acetate/hexane mixture to give the title compound (2.12 g, 89%) as a white amorphous.1H NMR (CDCl3) delta 3.68 (s, 3H), 6.95 (t, J = 8.1 Hz, IH), 7.03 (d, J = 8.1 Hz, IH), 7.18 (d, J = 8.1 Hz, IH). MS Calcd.: 243; Found: 244 (M+H) . |
7-Bromo-l-methyl-l, 3-dihydro-2H-benzimidazol-2-one (2.20 g, 9.69 mmol) was dissolved in 30 mL of phosphorous oxychloride and the mixture was heated at 110 0C for 2 days. The reaction allowed to cool to room temperature, poured into water with an ice, and stirred for 1 h. The aqueous solution was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuo to give 2.32 g of the title compound, which was used in the next reaction without further purification. MS Calcd. : 243; Found: 244 (M+H) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With tert.-butylnitrite; copper(ll) bromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 8h; | To a suspension of compound 5 (6.10 g, 37.4 mmol) and copper(II) bromide (4.20 g, 19.0 mmol) in N,N-dimethylformamide (30 mL) was added tert-butyl nitrite (5.43 mL, 41.1 mmol) at 0 C, and the mixture was stirred at room temperature for 8 h. The reaction mixture was passed through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine and concentrated in vacuo. The resulting solid was washed with ethanol-diethyl ether to give the title compound (3.53 g, 42%). 1H NMR (DMSO-d6) delta 3.56 (3H, s), 6.91 (1H, t, J = 8.0 Hz), 6.98 (1H, d, J = 8.0 Hz), 7.15 (1H, d, J = 8.0 Hz), 11.17 (1H, s). |
26% | A mixture of 7-amino-l-methyl-l, 3-dihydro-2tf- benzimidazol-2-one (20.0 g, 122 mmol) and t-butyl nitrite(19.0 g, 184 mmol) in acetonitrile (500 mL) was stirred at room temperature for 30 min. The reaction mixture was cooled at O0C. To the mixture was added portionwise copper (I) bromide (19.3 g, 135 mmol). The mixture was stirred at room temperature for 18 h. To the reaction mixture was added saturated aqueous ammonium chloride solution (400 mL) . The mixture was filtered, and washed with methanol. The filtrate was concentrated in vacuo. The residue was dissolved in water and ethyl acetate. The organic layer was separated and the aqueous part was further extracted with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on basic silica gel eluting with a 50% ethyl acetate/hexane mixture to give the title compound (7.30 g, 26%) as a brown amorphous . 1H NMR (CDCl3) delta 3.55 (s, 3H), 6.90 (t, J = 8.1 Hz, IH), 6.97 (d, J = 8.1 Hz, IH), 7.14 (d, J = 8.1 Hz, IH), 11.2 (br, IH) .MS Calcd.: 226; Found: 227 (M+H) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound 12C (454 mg, 2.0 mmol) was dissolved in DMF (10 mL) and the resulting solution was cooled to 0 C. NaH (88 mg, 2.2 mmol) was added carefully and the resulting reaction was stirred at 0 C for 10 minutes, then SEMCi (367 mg, 2.2 mmol) was added dropwise and the mixture was allowed to warm to room temperature on its own and stirred for about 15 hours. Saturated aqueous NH4CI solution was then added to quench the reaction and the mixture was extracted with EtOAc (40 mL x 3). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo and the resulting residue was purified using flash column chromatography (silica gel, 30% EtOAc/Hexanes) to provide compound 13A (688 mg) as oil. HPLC-MS tR = 2.32 min (UV254 nm); mass calculated for formula C14H2IBrN2O2Si 356.1 , observed LCMS m/z 329.1 (M+H - dimethyl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound 12C (363 mg, 1.6 mmol), K3PO4 (1.02 g, 4.8 mmol) and Pd(dppf)CI2 (5% mmol) were dissolved in 1 ,4 dioxane (5 mL) and the resulting solution was put under argon atmosphere. To this solution was added cyclopropane boronic acid (250 <n="76"/>mg, 2.9 mmol) and the reaction was heated to 90 C and allowed to stir at this temperature for 12 hours. The reaction mixture was diluted with EtOAc, washed sequentially with deionized water and brine, then dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified using flash column chromatography (silica gel, ethyl acetate as eluent) to provide compound 12D as a white solid. HPLC-MS tR - 1.34 min (UV254 nm); mass calculated for formula C11H12N2O 188.1, observed LCMS m/z 189.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100℃;Microwave irradiation; | General procedure: To a mixture of compound 5 (2.00 g, 12.3 mmol), X-Phos (0.292 g, 0.613 mmol), sodium tert-butoxide (2.94 g, 30.6 mmol) and tris(dibenzylidineacetone)dipalladium (0.224 g, 0.245 mmol) in 1,4-dioxane (25 mL) was added 4-bromoanisole (1.6 mL, 12.9 mmol) and heated to 100 C for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuo. The residue was powdered from diethyl ether to give the title compound (2.02 g, 61%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In 1,4-dioxane;Reflux; | General procedure: To a mixture of compound 5 (0.300 g, 1.84 mmol), S-Phos (0.0377 g, 0.0919 mmol), sodium tert-butoxide (0.350 g, 3.70 mmol), tris(dibenzylidineacetone)dipalladium (0.170 g, 0.180 mmol) and 1,4-dioxane (0.5 mL) was added 4-bromophenylmethylsulfone (0.520 g, 2.20 mmol), and the mixture was refluxed for 4 h. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate and ethyl acetate-tetrahydrofuran. The organic layer was concentrated in vacuo. The resulting solid was washed with ethyl acetate to give the title compound (0.357 g, 61%) as crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 1,1'-carbonyldiimidazole; In acetonitrile; at 85℃; for 12.0h;Inert atmosphere; | To a mixture of 3-bromo-N2-methyl-benzene-1,2-diamine (20.0 g, 99.4 mmol) in ACN (300 mL) was added CDI (32.2 g, 198 mmol). The reaction mixture was stirred at 85 C. for 12 hours under N2 atmosphere. On completion, the reaction mixture was concentrated in vacuo. The reaction mixture was diluted with water (200 mL), where a solid precipitate was formed, which was filtered off. The solid was washed with water (1 L) and dried in vacuo to give the title compound (20.0 g, 88% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) delta 11.17 (s, 1H), 7.14 (dd, J=1.2, 8.0 Hz, 1H), 7.00-6.95 (m, 1H), 6.93-6.87 (m, 1H), 3.55 (s, 3H). |
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