Ammonium Chloride → HCID 23152596, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (3.38 g, 10.0 mmol) obtained in the same manner as in the method described in WO03/010140 and 5-benzyloxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine (3.93 g, 12.1 mmol) in 1,2-dimethoxyethane (70 ml) and water (35 ml) were added sodium hydrogen carbonate (2.49 g, 30.0 mmol) and tetrakis(triphenylphosphine)palladium (582 mg, 0.50 mmol), and the mixture was stirred at 90° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The obtained crude product (6.20 g) was used for Step 5 without further purification.

Provenance & Evidence