chloromethylidene(dimethyl)azanium

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of 5-bromo-4,6-difluoro-1H-indole (285 mg, 1.23 mmol) in DMF (2 mL) was added N-(chloromethylidene)-N-methylmethanaminium (236 mg, 1.84 mmol) at room temperature. The reaction mixture was stirred for 30 min, and treated with additional N-(chloromethylidene)-N-methylmethanaminium (100 mg). The mixture was stirred for an additional 30 minutes at room temperature. The reaction mixture was then treated with 1N aqueous NaOH (2.5 mL) and water (2.5 mL). The mixture was stirred at 100° C. for 30 min. After cooling to room temperature, the solvents were evaporated in vacuo, and the residue was diluted with THF (2 mL) and water (2 mL). The resulting mixture was stirred at room temperature for 2 hours, and the resulting solids were collected by filtration. The solids were washed with water and heptanes and dried in vacuo to give the title compound (157 mg) as a brown solid. MS (ES+) 261.8 ((M+2)+H)+. The mixture was stirred for an additional 30 minutes at room temperature The mixture was stirred at 100° C. for 30 min the solvents were evaporated in vacuo the residue was diluted with THF (2 mL) and water (2 mL) The resulting mixture was stirred at room temperature for 2 hours the resulting solids were collected by filtration The solids were washed with water and heptanes dried in vacuo

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

実験手順: To a solution of 5-bromo-4,6-difluoro-1H-indole (285 mg, 1.23 mmol) in DMF (2 mL) was added N-(chloromethylidene)-N-methylmethanaminium (236 mg, 1.84 mmol) at room temperature. The reaction mixture was stirred for 30 min, and treated with additional N-(chloromethylidene)-N-methylmethanaminium (100 mg). The mixture was stirred for an additional 30 minutes at room temperature. The reaction mixture was then treated with 1 N aqueous NaOH (2.5 mL) and water (2.5 mL). The mixture was stirred at 100° C. for 30 min. After cooling to room temperature, the solvents were evaporated in vacuo, and the residue was diluted with THF (2 mL) and water (2 mL). The resulting mixture was stirred at room temperature for 2 hours, and the resulting solids were collected by filtration. The solids were washed with water and heptanes and dried in vacuo to give the title compound (157 mg) as a brown solid. MS (ES+) 261.8 ((M+2)+H)+. The mixture was stirred for an additional 30 minutes at room temperature The mixture was stirred at 100° C. for 30 min the solvents were evaporated in vacuo the residue was diluted with THF (2 mL) and water (2 mL) The resulting mixture was stirred at room temperature for 2 hours the resulting solids were collected by filtration The solids were washed with water and heptanes dried in vacuo