Sodium borohydride → HCID 178518420, compound

Participants

Reaction Steps

Cool a solution of 3-(6-fluorobenzofur-7-yl)-4-[1-(4-oxocyclohexyl)-1H-indol-3-yl]pyrrole-2,5-dione (395 mg, 0.89 mmol) in tetrahydrofuran (20 ml) in an ice bath. Add sodium borohydride (10 mg, 0.27 mmol) in one portion and stir for 5 minutes. Add another portion of sodium borohydride (10 mg, 0.27 mmol) and stir for 10 minutes in the ice bath. Quench the reaction is with water, then dilute with ethyl acetate, wash with water, 1N HCl, brine, dry over magnesium sulfate, filter, concentrate to a red foam. Purification by flash chromatography separates cis and trans isomers to give cis 3-(6-fluorobenzofur-7-yl)-4-[1-(4-hydroxycyclohexyl)-1H-indol-3-yl]pyrrole-2,5-dione and trans 3-(6-fluorobenzofur-7-yl)-4-[1-(4-hydroxycyclohexyl)-1H-indol-3-yl]pyrrole-2,5-dione as red solids. ES(M++H): 445.1.

Provenance & Evidence