Methanol → HCID 22100881, compound

Participants

Reaction Steps

Borane-THF ((1.0M soln in tetrahydrofuran, 27 mL) was added dropwise to a solution of N-[2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]ethyl]-4-pyridin-4-yl-butyramide (1.45 g, 2.96 mmol) in dry tetrahydrofuran (20 mL), and the solution was heated at reflux for 2 hours. At this time, methanol was added to quench excess borane, and the resulting solution was evaporated to dryness. The residue was dissolved in tetrahydrofuran (20 mL), and N,N-dimethylethanolamine (8.9 mL, 88.86 mmol) was added. The solution was heated at reflux for 2.5 hr and then concentrated to dryness. The crude material was purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (1.0 g, 71%). m/e=476 (M+H)

Provenance & Evidence