1,2-Dichloroethane → 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid methylester

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Reaction Steps

To a solution of 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid (1.7 grams, 5.00 mmol) in methylene chloride (50 mL), was added 4-dimethylaminopyridine (0.67 grams, 5.50 mmol), 1,2-dichloroethane (1.06 grams, 5.50 mmol), triethylamine (0.73 mL, 5.25 mmol) and 4,4,4-trifluoro-2-methylbutylamine hydrochloride (0.93 grams, 5.25 mmol). The resulting solution was stirred 12 hours, at room temperature, then diluted with methylene chloride. The solution was washed with 1 M hydrochloric acid (aq), then the organics were dried over magnesium sulfate. Concentration in vacuo followed by trituration of the crude product in a 2:1 ratio of ether:hexanes gave 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid methylester (1.88 grams, 82% yield).

Provenance & Evidence