Potassium Carbonate → methyl 6-chloro-5-(2'-hydroxybiphenyl-4-yl)-1H-indole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A glass tube was charged with 4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-ol (86.2 mg, 0.29 mmol), methyl 5-bromo-6-chloro-1H-indole-3-carboxylate (84 mg, 0.29 mmol), toluene (1.2 mL), THF (0.6 mL), EtOH (0.6 mL), and 2.0 M potassium carbonate solution (0.6 mL, 1.2 mmol). Nitrogen was then bubbled through the mixture for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (28 mg, 0.032 mmol) was added. The tube was sealed and heated to 115° C. for 2 hours. The reaction was cooled to room temperature, opened, and neutralized with 1.0 M sodium hydrogensulfate then diluted with ethyl acetate. The layers were separated and the aqueous extracted with ethyl acetate (×2). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash column chromatography (20% to 100% ethyl acetate/heptane) was then used to to provide the title compound as a white solid (80 mg, 73% yield). MS (ES−) 376.1 (M−H). 1H NMR (500 MHz, DMSO-d6) δ 12.09 (br. s., 1 H), 9.60 (s, 1 H), 8.19 (s, 1 H), 7.98 (s, 1 H), 7.68 (s, 1 H), 7.65 (d, 2 H), 7.47 (d, 2 H), 7.34 (dd, 1 H), 7.19 (dt, 1 H), 6.98 (d, 1 H), 6.91 (dt, 1 H), 3.81 (s, 3 H).

Provenance & Evidence