Sulfuric acid magnesium salt (1:1) → 2-(3,5-Dimethylphenyl)-3-{2-[(5-pyridin-3-yl-thiophen-2-ylmethyl)amino]-ethyl}-1H-indole-5-carboxylic acid diisopropylamide

Participants

Reaction Steps

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisopropylamide in a mixture of dry chloroform and methanol at 0° C. is added magnesium sulfate followed by 5-pyridin-3-yl-thiophene-2-carbaldehyde and the mixture stirred at low temperature. After 40 minutes, acetic acid is added followed by a solution of sodium cyanoborohydride and the mixture allowed to warm to room temperature. After completion, the reaction is quenched by the addition of saturated aqueous sodium bicarbonate, extracted with methylene chloride and the combined organics washed sequentially with water and brine. Purification of the concentrate by preparative tic on silica gel gives the title compound.

Provenance & Evidence