Potassium Carbonate → HCID 86698602, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-6-chloro-1H-indole-3-carbaldehyde (150 mg, 0.44 mmol), 1-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-3-fluorophenyl]cyclobutanol (181 mg, 0.652 mmol), 2M aqueous potassium carbonate (0.87 mL, 1.74 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (18 mg, 0.022 mmol) in ethanol (4 mL) was sealed in a reaction vessel and heated thermally to 130° C. for 3 hours. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine and dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified using flash chromatography eluting with heptanes/ethyl acetate (0:100 to 60:40) to give the title compound (57 mg, 58%). 1H NMR (500 MHz, DMSO-d6) δ 12.18-12.38 (m, 1H), 9.95 (s, 1H), 8.40 (s, 1H), 8.04 (s, 1H), 7.73 (s, 1H), 7.34-7.50 (m, 3H), 5.68 (s, 1H), 2.40-2.47 (m, 2H), 2.21-2.38 (m, 2H), 1.90-1.99 (m, 1H), 1.68-1.81 (m, 1H).

Provenance & Evidence