Dichloromethane → HCID 57290459, compound

Participants

Reaction Steps

N-Chlorosuccinimide (0.313 g) was added in one portion to a stirred solution of methyl 4-[5-[2-(N',N'-dimethylureido)propyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate (0.5 g) in dichloromethane (25 ml). After 30 minutes, the solvent was evaporated, and the product isolated by flash chromatography, eluting with 3:7 ethyl acetate:toluene, to give methyl 4-[2,6-dichloro-5-[2-(N',N'-dimethylureido)propyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate (60%) as a white solid; mp 175°-176° C.; NMR (300 MHz, DMSO-d6): 1.00 (d, 3H, CH3), 2.61 (s, 6H), 2.82 (d, 2H), 3.72 (s, 3H, CH3), 3.83 (s, 3H, OCH3), 3.85-3.96 (m, 4H), 4.00 (s, 2H), 5.91 (d, 1H, NH), 6.99 (d, 1H), 7.33 (s, 1H), 7.38-7.50 (m, 2H), 7.61 (s, 1H).

Provenance & Evidence