Water → HCID 9827187, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(8-cyano-1-oxo-3-phenyl-1,2-dihydropyrido[3,4-b]indol-2-yl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.5 g) and sodium hypophosphite hydrate (0.35 g) in pyridine (3 mL), acetic acid (1.5 mL), and H2O (1.5 mL) was added a small amount of Raney nickel (50% slurry in water, pH greater than 9) and the resulting mixture was heated at 60° C. for 1 hour. Additional sodium hypophosphite hydrate (0.1 g) was added and the mixture was heated at 60° C. for 1 hour. The reaction mixture was diluted with methanol, filtered through diatomaceous earth, evaporated, and diluted with ethyl acetate. The resulting solution was washed with 1N hydrochloric acid, dried, and evaporated to give the aldehyde (0.4 g) as a yellow solid; TLC: Rf =0.45, methanol:dichloromethane (5:95);

Provenance & Evidence