2-(5-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide → 2-(5-(5-(aminomethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3 b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

Participants

Reaction Steps

To a solution of the 2-(5-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide, (9-1a) (110 mg, 187 mmol) 10-1a in ethanol (5.0 ml) was added Raney Nickel (2.197 mg, 0.037 mmol) Ammonium hydroxide (0.260 μl, 1.871 μmol) was added and the flask evacuated and backfilled with hydrogen gas 3 times. The mixture was stirred under hydrogen for 17 hrs. The reaction was purged with nitrogen, diluted with ethanol and filtered through a pad of celite. The filtrate was concentrated and oil purified by Reverse phase HPLC (Water:ACN w/0.1% TFA, C-18, 35-65% gradient). The pure fractions concentrated to remove acetonitrile and mixture neutralized with saturated sodium bicarbonate. The product was extracted with ethyl acetate (3×20 mL). The organics were dried with sodium sulfate, filtered and concentrated to afford the product 10-1b as a solid (50 mg, 47%).

Provenance & Evidence