Diethyl Ether → HCID 59205406, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.0M methyl magnesium bromide in diethyl ether (0.5 ml, 1.50 mmol) was added dropwise to a solution of 3-{[5-chloro-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carbonyl]amino}propionic acid ethyl ester (Example 15) (200 mg, 0.42 mmol) in THF (4 ml) under nitrogen, maintaining temperature between 0 and 5° C. After stirring at 0° C. for 2 h, the reaction was quenched by slowly pouring the reaction mixture into water (2.0 ml). Volatile solvents were then removed under reduced pressure and the aqueous residue filtered. Purification was achieved by chromatography on silica using heptane:ethyl acetate (9:1 followed by 4:1) as eluent to afford 5-chloro-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (3-hydroxy-3-methylbutyl)amide as an off-white solid (28 mg, 15%).

Provenance & Evidence