Hydrochloric Acid → 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamide

Participants

Reaction Steps

To 4-methoxy-1H-indole-2-carboxylic acid (0.844 g, 4.42 mmol) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1 g, 4.01 mmol) in dichloromethane (20 ml) at 0° C. under a nitrogen atmosphere were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) hydrochloride (0.846 g, 4.42 mmol) and 1-hydroxy-7-azabenzotriazole (0.546 g, 4.01 mmol). The resulting brown solution was stirred at room temperature overnight. The reaction mixture was poured in water, the solids were collected by filtration and washed with some water. The solid was dried in a vacuum oven at 40° C. The solids were suspended in acetonitril (50 ml) and methanol (10 ml) and heated at 60° C. for 1 hour. The solids were collected by filtration and washed with hot acetonitril. Then the solids were stirred over night in dichloromethane. The mixture was filtered over a filter. The filtrate was concentrated in vacuo and gave 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamide (1.1 g).

Provenance & Evidence