1-Hydroxybenzotriazole → N-[6-(Dimethylamino)pyridin-3-yl]-5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

Participants

Reaction Steps

Compound No. 7 was prepared according to a process similar to that described in stage 5.4, by reacting 0.3 g (0.88 mmol) of 5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid, prepared according to the protocol described in stage 3.6, with 181 mg (1.32 mmol) of 3-amino-6-(dimethylamino)pyridine in the presence of 185 mg (0.97 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) and of 131 mg (0.97 mmol) of 1-hydroxybenzotriazole (HOBT) in 10 ml of dimethylformamide. The product obtained is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and acetone. The solid obtained after evaporation of the solvent under reduced pressure is recrystallized from isopropyl alcohol. 200 mg of the expected product are thus isolated.

Provenance & Evidence