4-Fluorophenylboronic acid → 2-Amino-6-(4-fluoro-phenyl)-benzo[b]thiophene-3-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of 1d (200 mg, 0.67 mmol) in 1,4-dioxane/water (40 mL, 3:1) was added 4-fluorophenylboronic acid (209 mg, 1.34 mmol), NaHCO3 (225 mg, 2.68 mmol) and Pd(PPh3)4 (9% Pd, 79 mg, 0.067 mmol). The resultant mixture was heated at 110° C. for 1 h, diluted with brine solution (50 mL) and extracted with ethyl acetate (50 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4:1) then provided the title compound (190 mg, 90%) as a pink sticky oil: MS (ES) m/z 316 (M+H)+; 1H NMR (400 MHz, CDCl3) δ8.16 (d, J=8.4 Hz, 1H), 7.69 (s, 1H), 7.62 (m, 2H), 7.50 (d, J=8.4 Hz, 1H), 7.15 (m, 2H), 6.58 (brs, 2H), 4.46 (q, J=7.2 Hz, 2H), 1.50 (t, J=7.2 Hz, 3H).

Provenance & Evidence