1-Propanol, 3-amino-2,2-dimethyl- → 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid (3-hydroxy-2,2-dimethylpropyl)amide

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Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.14 g, 0.57 mmol) and 1-hydroxybenzotriazole hydrate (HOBT) (0.1 μg, 0.59 mmol) were added to a solution of 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid (0.20 g, 0.67 mmol) in DCM (10 ml). After stirring for 10 min, 3-amino-2,2-dimethylpropan-1-ol (0.083 g, 0.80 mmol) was added. After stirring for 17.5 h, water (10 ml) was added, the layers separated, the organic phase washed with water (3×15 ml) and dried with magnesium sulfate. Purification was achieved by silica chromatography using DCM:methanol (3:1) as eluent. Crystallisation of the crude product afforded 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid (3-hydroxy-2,2-dimethylpropyl)amide as a white solid (0.100 g, 43%).

Provenance & Evidence