Methyl iodide → HCID 22485710, compound

Participants

Reaction Steps

Sodium hydride (0.19 g of 60% suspension in oil) was suspended in dry THF (10 ml). 6-Chloroindole-3-acetic acid (SR058)(100 mg, 0.48 mmol) in THF (5 ml) was added dropwise and the mixture then stirred for 10 minutes. Iodomethane (0.34 g, 2.4 mmol) was then added, and the mixture stirred overnight. Excess sodium hydride was carefully destroyed by dropwise addition of water, and then the mixture was acidified (1M HCl) and extracted with ethyl acetate (3×50 ml), the organic layers dried over MgSO4, and the solvent evaporated to give a brown powder, yield 75 mg, 70%, m.p. 130-132° C. dec.; m/z 225, 223 (M+), 180, 178 (M+-CO2H); δH/ppm 7.46-6.92 (4H, m, Ar—H), 3.77 (3H, s, N—Me), 3.70 (2H, s, ArCH2).

Provenance & Evidence