Acetic Acid → N-(3-(5-fluoro-1-methylindolin-6-yl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methylpiperidine-4-sulfonamide

Participants

Reaction Steps

To a stirred solution of N-(3-(5-fluoro-1-methylindolin-6-yl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidine-4-sulfonamide, hydrochloride (D39) (248 mg, 0.488 mmol) in MeOH (8 mL) at RT was added acetic acid (0.279 mL, 4.88 mmol), formaldehyde (37% solution in water) (0.218 mL, 2.93 mmol) and sodium cyanoborohydride (307 mg, 4.88 mmol). The reaction mixture was stirred at RT for an hour. The reaction mixture was concentrated in vacuo. The residue was passed through SCX cartridge (eluted with MeOH followed by 2M NH3 in MeOH solution; 100 mL each). The basic fractions were concentrated in vacuo to afford a material which was purified using chromatography on silica, eluted with 0-10% MeOH in DCM to afford the title compound (84 mg). LCMS (A): m/z (M+H)+ 486, C25H32FN5O2S requires 485 (acidic).

Provenance & Evidence