4-bromo-N-methylbenzamide

反応条件: temp:60.01; pressure:0.00; stir:

実験手順: Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 1:1) as the eluent.

反応条件: temp:60.01; pressure:0.00; stir:

実験手順: Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 1:1) as the eluent.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromobenzoic acid (300 mg, 1.49 mmol), hydroxybenzotriazole (1.1 eq), 1(3-dimethylaminoprpyl)-3-ethylcarbodiimide HCl (1.1 eq) and diisopropylethylamine (2 eq) in DMF (2 mL) was stirred at rt for 20 min. Methylamine (1 eq) was added and the reaction stirred at rt for 16 h then quenched with saturated aqueous sodium hydrogencarbonate solution and extracted into ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give 4-bromo-N-methylbenzamide. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.56 (s, 1H), 8.38 (s, 1H), 8.32-8.36 (m, 2H), 8.05-8.09 (m, 2H), 7.94 (s, 1H), 7.67 (s, 1H), 3.87 (s, 3H), 2.83 (d, 3H); LC-MS method B, (ES+) 349.0, RT=6.68 min. then quenched with saturated aqueous sodium hydrogencarbonate solution extracted into ethyl acetate The organic layer was washed with brine dried (MgSO4) concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromobenzoic acid (300 mg, 1.49 mmol), hydroxybenzotriazole (1.1 eq), 1(3-dimethylaminoprpyl)-3-ethylcarbodiimide HCl (1.1 eq) and diisopropylethylamine (2 eq) in DMF (2 mL) was stirred at rt for 20 min. Methylamine (1 eq) was added and the reaction stirred at rt for 16 h then quenched with saturated aqueous sodium hydrogencarbonate solution and extracted into ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give 4-bromo-N-methylbenzamide. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.56 (s, 1H), 8.38 (s, 1H), 8.32-8.36 (m, 2H), 8.05-8.09 (m, 2H), 7.94 (s, 1H), 7.67 (s, 1H), 3.87 (s, 3H), 2.83 (d, 3H); LC-MS method B, (ES+) 349.0, RT=6.68 min. then quenched with saturated aqueous sodium hydrogencarbonate solution extracted into ethyl acetate The organic layer was washed with brine dried (MgSO4) concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromobenzoyl chloride (5.6 g) in 50 mL of tetrahydrofuran was cooled to 0° C. and treated with aqueous methylamine (5 mL of 40%). After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 16 hours. At the end of this period, the reaction mixture was diluted with water, extracted with ethyl acetate and the organic layer was washed with 10% HCl followed by sodium carbonate. Upon drying over magnesium sulfate and evaporation, a white solid was obtained (4.64 g); MS: 214; NMR: 3.0 (d, J=5, 3), 6.2 (br, 1), 7.5-7.6 (m, 2), 7.6-7.7 (m, 2). After the addition extracted with ethyl acetate the organic layer was washed with 10% HCl Upon drying over magnesium sulfate and evaporation a white solid was obtained (4.64 g)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromobenzoyl chloride (5.6 g) in 50 mL of tetrahydrofuran was cooled to 0° C. and treated with aqueous methylamine (5 mL of 40%). After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 16 hours. At the end of this period, the reaction mixture was diluted with water, extracted with ethyl acetate and the organic layer was washed with 10% HCl followed by sodium carbonate. Upon drying over magnesium sulfate and evaporation, a white solid was obtained (4.64 g); MS: 214; NMR: 3.0 (d, J=5, 3), 6.2 (br, 1), 7.5-7.6 (m, 2), 7.6-7.7 (m, 2). After the addition extracted with ethyl acetate the organic layer was washed with 10% HCl Upon drying over magnesium sulfate and evaporation a white solid was obtained (4.64 g)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromobenzoic acid (300 mg, 1.49 mmol), hydroxybenzotriazole (1.1 eq), 1(3-dimethylaminoprpyl)-3-ethylcarbodiimide HCl (1.1 eq) and diisopropylethylamine (2 eq) in DMF (2 mL) was stirred at rt for 20 min. Methylamine (1 eq) was added and the reaction stirred at rt for 16 h then quenched with saturated aqueous sodium hydrogencarbonate solution and extracted into ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give 4-bromo-N-methylbenzamide. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.56 (s, 1H), 8.38 (s, 1H), 8.32-8.36 (m, 2H), 8.05-8.09 (m, 2H), 7.94 (s, 1H), 7.67 (s, 1H), 3.87 (s, 3H), 2.83 (d, 3H); LC-MS method B, (ES+) 349.0, RT=6.68 min. then quenched with saturated aqueous sodium hydrogencarbonate solution extracted into ethyl acetate The organic layer was washed with brine dried (MgSO4) concentrated in vacuo