Potassium Carbonate → HCID 59712247, compound

Participants

Reaction Conditions

Reaction Steps

2-(1H-Pyrrol-3-yl)pyridine (2.0 g, 17 mmol), 1-bromo-3,5-diflurobenzene (6.6 g, 34 mmol), potassium carbonate (2.4 g, 34 mmol) were combined in DMF (30 mL) under argon. The reaction mixture was heated at 140° 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 (300 mL), and washed with H2O (3×300 mL), brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a dark oil which solidified when pumped down under high vacuum. The crude product was purified by column chromatography eluting with 2:8 EtOAc:hexanes to afford 2-[1-(3-bromo-5-fluorophenyl)-1H-pyrrol-3-yl]pyridine (1.5 g, 35% yield) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.61-8.62 (d, 1H), 8.50-8.53 (t, 1H), 8.40 (s, 1H), 8.35-8.36 (d, 1H), 7.78-7.81 (m, 2H), 7.57-7.62 (m, 1H), 7.54-7.57 (d, 1H), 7.43-7.46 (d, 1H), 7.11 (s, 1H), MS 319.1 (M++H).

Provenance & Evidence