Tetramethylammonium Triacetoxyborohydride (>90%) → 4-phenoxy-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)-1H-pyrazolo[4,3-c]pyridin-3-amine

Participants

Reaction Steps

A solution of the compound prepared in Example 436 (0.053 g) and the compound prepared in Example 214 (0.039 g) in acetonitrile (1 mL) was stirred at room temperature for 30 minutes. Tetramethylammoniumtriacetoxy borohydride (0.094 g) was added and stirring at room temperature continued for 1 hour. The reaction mixture was quenched with aqueous saturated sodium bicarbonate. After stirring at room temperature for 20 minutes, hopeful product was extracted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, dried, evaporated in vacuo to an oil that was purified by column chromatography on silica gel (1-5% methanol in dichloromethane) to provide the title compound (0.008 g) with the following physical data.

Provenance & Evidence