Benzyl Alcohol → HCID 68682318, compound

Participants

Reaction Steps

To the suspension of 105 mg (0.70 mmol) (cyanomethyl)trimethylphosphonium chloride (prepared according to Tetrahedron Lett. 1996, 37 (14), 2459-62) in 1 mL toluene, 1.39 mL (0.70 mmol; 0.5M solution in toluene) potassium bis(trimethylsilyl)amide was added. After 10 min., 71 μL (74 mg, 0.70 mmol) benzylalcohol and 0.15 g (0.35 mmol) [2-(1,1-dioxo-thiomorpholine-4-carbonyl)-1H-indol-5-yl]-(4-isopropyl-piperazin-1-yl)-methanone (example 1) were added and the suspension was stirred for 1 h at reflux temperature. After cooling to room temperature the reaction mixture was evaporated to dryness, the residue was taken up in dichloromethane, filtered and the filtrate was evaporated. The crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (19:1:0.1 v/v) as eluant to give 118 mg (65%) of the desired compound as a colorless foam.

Provenance & Evidence