Potassium Carbonate → 5-{4-[1-(hydroxymethyl)cyclopropyl]phenyl}-6-methyl-1H-indole-3-carbaldehyde

Participants

Reaction Steps

A solution of 5-bromo-6-methyl-1H-indole-3-carbaldehyde (200 mg, 0.84 mmol) and {1-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]cyclopropyl}methanol (242 mg, 0.93 mmol) in toluene (6 mL) and EtOH (2.0 mL) was added to a solution of potassium carbonate (350 mg, 2.52 mmol) in water (1.0 mL) and Pd(dppf)Cl2 (34 mg, 0.042 mmol) at room temperature under N2. TLC (petroleum ether/EtOAc=1:1) showed the reaction was complete. The reaction was cooled to room temperature, and extracted with ethyl acetate (20 mL×3). The organic layers were washed with brine (20 mL), dried over sodium sulfate and concentrated to give a crude ARRR!!!!, which was purified by column chromatography to give the title compound (190 mg, 74%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 9.83 (s, 1 H), 8.05 (s, 1 H), 7.93 (s, 1 H), 7.41 (d, 2 H), 7.37 (s, 1 H), 7.27 (d, 2 H), 3.69 (s, 2 H), 2.31 (s, 3 H), 0.89 (d, 4 H).

Provenance & Evidence