Sodium Iodide → HCID 22859588, compound

Participants

Reaction Steps

5-Bromo-3-(pyrrolidin-2(R)-ylmethyl)-1H-indole (1.84 g, 6.3 mmol) (see Preparation 55), cyclopropylmethyl bromide (0.67 ml, 6.9 mmol), sodium carbonate (0.73 g, 6.9 mmol) and sodium iodide (1.0 g, 6.7 mmol) in 1,2-dimethoxyethane (10 ml) was refluxed under nitrogen for 14 hours. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate and aqueous sodium carbonate. The organic phase was washed with more aqueous sodium carbonate, dried (Na2SO4) and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide (90:10:0.05) to yield the title compound as a foam (2.09 g). Found: C,61.22; H,6.40; N,8.39. C17H21BrN2 requires: C,61.26; H,6.35; N,8.41%.

Provenance & Evidence