Methanol → HCID 69303781, compound

Participants

Reaction Conditions

Reaction Steps

2-[1-(3-Bromo-5-fluorophenyl)-1H-pyrrol-3-yl]pyridine (463 mg, 1.46 mmol), 4-methylpyridin-3-ylboronic acid (200 mg, 1.46 mmol), potassium carbonate (500 mg, 3.0 mmol) were combined in toluene:methanol (10:2 mL) under argon and Pd(PPh3)4 (231 mg, 0.2 mmol) was added and the argon flow was continued for 10 min. The reaction mixture was heated at 90° C. overnight. The reaction mixture was allowed to cool to ambient temperature. TLC analysis showed no starting material present. The reaction mixture was diluted with EtOAc (100 mL), and washed with H2O (3×100 mL), brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a dark oil. The crude product was purified by column chromatography eluting with 3.5:6.5 EtOAc: Hexane to afford 4-[3-fluoro-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)phenyl]-3-methylpyridine (280 mg, 59% yield) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.91 (s, 1H), 8.81-8.82 (d, 1H), 8.62-8.63 (d, 2H), 8.51-8.54 (t, 1H), 8.40-8.42 (d, 1H), 8.13-8.15 (d, 1H), 7.75-7.81 (m, 3H), 7.70 (s, 1H), 7.40-7.42 (d, 1H), 7.17 (s, 1H), 2.75 (s, 3H). MS 330.1 (M++H).

Provenance & Evidence