Sodium Hydroxide → 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

Participants

Reaction Steps

A 1M solution of NaOH (809 μL, 0.809 mmol) was added to a solution of 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (135 mg, 0.270 mmol) in 4:1 THF/MeOH (1.4 mL, 0.2M). The reaction mixture was stirred at room temperature for 30 minutes. The majority of the organic solvents were removed in vacuo. The resulting residue was acidified with 1N HCl (0.8 mL) and then partitioned between EtOAc (30 mL) and water (10 mL). The organic layer was washed with water (3×10 mL), brine (10 mL), dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with minimal CH2Cl2, and the precipitate was filtered and rinsed with Et2O to afford 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide as a solid (48 mg, 45% yield for 2 steps).

Provenance & Evidence