Ethyl Acetate → [4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanol

Participants

Reaction Steps

To a solution of 4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde (5-2, 0.317 g, 0.870 mmol) in methanol (5 mL) was added sodium borohydride (0.033 g, 0.870 mmol) at 0° C. After 10 minutes, the reaction mixture was poured into ethyl acetate, and the organic layer was washed with a saturated solution of sodium bicarbonate, water, then brine, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. Purification by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) gave the title compounds as a solid. HRMS (M+H+): calculated=367.1554, observed=367.1547.

Provenance & Evidence