Potassium Carbonate → HCID 86698769, compound

Participants

Reaction Steps

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (152 mg, 0.577 mmol) in anhydrous dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (170 mg, 1.33 mmol). The reaction mixture was stirred at room temperature for 20 mins. A thick solution was observed after 20 mins. 2 N potassium carbonate (400 mg, 2.90 mmol), 1-(4-bromophenyl)cyclopropanecarboxylic acid (137 mg, 0.568 mmol) and Pd(dppf)Cl2 (50 mg, 0.068 mmol) were then added. The reaction was degassed with N2 for 2 minutes. The reaction was then heated to 90° C. for 30 minutes. The mixture was poured into water (60 mL) and the layers separated. The aqueous layer was extracted with ethyl acetate (50 mL×2). The aqueous phase was acidified to pH=5 with 1 N HCl and then extracted with ethyl acetate (50 mL×3). The combined organic phases were washed with brine (50 mL), dried and concentrated to give the title compound (253 mg, quantitative yield) as a brown oil, which was used in the next step without further purification.

Provenance & Evidence