Methyl iodide → Benzyl 1-methyl-1H-indole-6carboxylate

Participants

Reaction Steps

Sodium hydride (1.03 g of a 60% dispersion in paraffin oil) was added portionwise to a stirred solution of benzyl 1H-indole-6-carboxylate (from (a), 5.4 g, 21.5 mmol) in tetrahydrofuran (80 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred for 2 h, then methyl iodide (2.04 ml, 32.6 mmol) was added dropwise. The solution was allowed to warm to room temperature over 12 h. The reaction was quenched by the slow addition of ice cold water and the tetrahydrofuran was removed in vacuo. The product was extracted from saturated sodium chloride solution (300 ml) with dichloromethane (2×300 ml) and the organics were dried (MgSO4). The dried organics were filtered through a 5 cm plug of silica in a sintered funnel and concentrated in vacuo to give the subtitle compound as a white solid (5.1 g).

Provenance & Evidence