Sodium borohydride → HCID 67994748, compound

Participants

Reaction Steps

A mixture of 3-(1-aminoxycarbonyl)-7-cyanomethyl)-9H-pyrido[3,4-b]indole-4-yl-2-methylaniline 7 (40 mg, 0.112 mmol), 5-chloro-2-formylbenzoic acid (51.6 mg, 0.28 mmol) and 4 angstrom molecular sieves (0.5 g) in methanol (15 mL) was stirred at RT for 24 h. After that the mixture was cooled to −20° C. and sodium borohydride (29.6 mg, 0.78 mmol) was added and the reaction mixture was allowed to warm up to 10° C. The solvent was removed under reduced pressure, quenched with saturated NH4Cl solution (5 ml) and extracted with EtOAc (2×10 ml). Combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated. The crude product obtained was purified by silica gel column chromatography eluting with 5% MeOH in CHCl3 to give the desired product (10 mg, 0.019 mmol, 17% yield) as a yellow sticky solid.

Provenance & Evidence