4-Fluoroiodobenzene → HCID 10500757, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-benzyl-N-methyl-2-(5-chloro-3-1H-indolyl)ethylamine (16 g, 0.054 mol), 4-fluoro-iodobenzene (14.3 g, 0.064 mol), K2CO3 (11.1 g, 0.080 mol) and 1-methyl-2-pyrrolidinone (200 mL) was heated at 165° C. for 8 h. After cooling to room temperature water (250 mL) was added and the thus formed mixture was extracted with diethyl ether (2×300 mL). The combined organic phases were washed with brine (3×500 mL) and dried (Na2SO4). Evaporation of the solvent afforded an oil that was purified by column chromatography (eluted with ethyl acetate/heptane 1:3) affording pure title compound as an oil: 13.7 g (26%) 1H NMR (CDCl3) δ 2.35 (s, 3 H), 2.70-2.80 (m, 2 H), 2.90-3.00 (m, 2 H), 3.60 (s, 2 H), 7.05-7.40 (m, 12 H), 7.55 (broad s, 1 H).

Provenance & Evidence