Phosphorus oxychloride → HCID 86614344, compound

Participants

Reaction Steps

Step a): To a stirred solution of Intermediate 1 (25 mg, 0.085 mmol), cyclohexyl-phenylacetic acid (27.7 mg, 0.127 mmol) and DIEA (73 μl, 0.424 mmol) in dichloromethane (1 ml) is added POCl3 (9 μl, 0.093 mmol). The resulting yellow reaction mixture is stirred at rt overnight, then saturated aqueous NaHCO3 solution (2 ml) is added. The organic layer is separated and washed with water (2 ml). Evaporation of the solvent gave a crude that is purified by silica gel column chromatography (hexane/EtOAc 3:1) affording ethyl [2-(2-cyclohexyl-2-phenyl-acetyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetate as a white solid (29 mg) in 74% yield: tR (LC-2) 2.74 min; ESI-MS (positive ion): m/z 459.25 [M+H]+ (calcd 458.59 for C29H34N2O3).

Provenance & Evidence