Potassium Carbonate → HCID 178498872, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-3-(4-bromophenyl)cyclobutanol (200 mg, 0.88 mmol) in toluene/ethanol (4 mL, v/v=1/1) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (296 mg, 0.968 mmol), potassium carbonate (360 mg, 2.64 mmol), water (1 mL) and Pd(dppf)C12 (46 mg, 0.06 mmol) under nitrogen. The mixture was stirred at 110° C. for 2 hours. The mixture was diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by silica gel combiflash to give the title compound (190 mg, 61%) as a light yellow solid. 1H NMR (500 MHz, CD3OD) δ 8.02 (s, 1 H), 8.01 (s, 1 H), 7.60 (s, 1 H), 7.40-7.35 (m, 4 H), 4.52 (m, 1 H), 3.88 (s, 3 H), 3.66 (m, 1 H), 2.57-2.44 (m, 4 H).

Provenance & Evidence