Potassium Carbonate → HCID 68496157, compound

Participants

Reaction Steps

To a mixture of 6-hydroxy-1-methyl-1H-indole-2-carboxylic acid (12.27 g, 64.2 mmol) and piperazine-1-carboxylic acid tert-butyl ester (14.34 g, 77.0 mmol) in DMF (80 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (18.4 g, 96.0 mmol) and 1-hydroxybenzotriazole monohydrate (11.6 g, 75.7 mmol) under ice cooling, and the mixture was stirred at room temperature overnight. The mixture was evaporated under reduced pressure, and then water and AcOEt were added to the residue. The organic layer was separated and washed with 1M HCl, saturated aqueous NaHCO3 and brine, dried over anhydrous magnesium sulfate and evaporated. To a mixture of the residue and 2-chloro-5-nitropyridine (10.05 g, 63.4 mmol) in DMF (80 mL) was added K2CO3 (11.92 g, 86.2 mmol) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure, and then water and Et2O were added to the residual mixture. After the mixture was stirred for 1 hour, the precipitate was collected by filtration and dried to afford 23.2 g of the title compound as a yellow powder.

Provenance & Evidence