Propargyl bromide → 3-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole

Participants

Reaction Steps

To a solution of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime (170 mg, 0.59 mmol) in dichloromethane (5 ml) cooled to 0° C., was added N-chlorosuccinimide (119 mg, 0.89 mmol) and the mixture allowed to warm to room temperature with stirring for 1 h. Propargyl bromide (8 μl, 0.65 mmol) and triethylamine (9 μl, 0.65 mmol) were added and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography eluting with 60-80% (v/v) dichloromethane in n-heptane to afford 3-(5-bromomethyl-isoxazol-3-yl)-1-cyclohexylmethyl-7-methoxy-1H-indole (150 mg, 0.37 mmol) as a yellow solid.

Provenance & Evidence