3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → HCID 12114959, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate (0.348 g, 1.00 mmol) in methyl sulfoxide (20 mL) was added 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.793 g, 4.00 mmol) and the reaction mixture was heated to 80° C. for 12 h. The reaction mixture was allowed to cool to room temperature and was diluted with ethyl acetate (200 mL), washed with water (2×100 mL), aqueous sodium chloride (100 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 4:1) followed by recrystallization from ethanol provided 0.254 g (68%, 40% ee) of 3-(1-{[(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]methyl}-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole as a yellow crystalline powder. [α]D25=−28.22 (c 9.92 in chloroform, 40% ee); Rf=0.34 (silica, ethyl acetate:hexanes 4:1); mp 190-194° C. dec; Anal. Calcd. for C24H26N2O2.0.1 H2O: C, 76.61; H, 7.02; N, 7.44. Found: C, 76.42; H, 6.99 N, 7.43.

Provenance & Evidence