Water → 5-Bromo-4,6-difluoro-1H-indole-3-carbaldehyde

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)+.

1. stirringThe mixture was stirred for an additional 30 minutes at room temperature
2. stirringThe mixture was stirred at 100° C. for 30 min
3. customthe solvents were evaporated in vacuo
4. additionthe residue was diluted with THF (2 mL) and water (2 mL)
5. stirringThe resulting mixture was stirred at room temperature for 2 hours
6. filtrationthe resulting solids were collected by filtration
7. washThe solids were washed with water and heptanes
8. customdried in vacuo

ORD record

ord-df0cc8852dbd41a3a543556a0a7fb273

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2