Potassium Carbonate → HCID 59418773, compound

Participants

Reaction Steps

Tert-butyl 7-(6-(methoxycarbonyl)-5-(trifluoromethylsulfonyloxy)pyridin-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (29E) (40 mg, 0.077 mmol), phenylboronic acid (11 mg, 0.093 mmol, 1.2 eq), K2CO3 (27 mg, 0.19 mmol), tetrabutylammonium bromide (2.5 mg, 0.0077 mmol), and dichlorobis(triphenylphosphine)palladium(II) (2.2 mg, 0.003 mmol) in 1,4-dioxane (0.5 mL) and water (0.25 mL) was heated to 90° C. for 75 minutes, cooled to rt, diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 88:12-82:18, to provide the desired product tert-butyl 7-(6-(methoxycarbonyl)-5-phenylpyridin-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (29G): 1H NMR (300 MHz, CDCl3) δ 8.41 (1H, d), 7.88 (1H, d), 7.80 (1H, d), 7.71 (1H, dd), 7.48-7.37 (5H, m), 7.19 (1H, d), 3.80-3.70 (5H, m), 2.82 (2H, t), 1.96 (2H, m), 1.57 (9H, s).

Provenance & Evidence