Sodium Carbonate → 6-Fluoro-2,3'-bipyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-6-fluoro-pyridine (0.436 mL, 3.31 mmol) (Oakwood,), 3-pyridylboronic acid (448 mg, 3.65 mmol) (Combi-Blocks Inc.), and tetrakis(triphenylphosphine)palladium (0) (77 mg, 0.066 mmol) (Strem Chemicals) was purged with argon and dioxane (10 mL) and a 1 M solution of sodium carbonate (4.97 mL, 4.97 mmol) were added. The mixture was heated in a microwave at 110° C. for 30 min. The cooled reaction mixture was treated with 1 N NaOH and extracted with EtOAc (30 mL), washed with brine and dried over MgSO4, filtered and concentrated. Purification on the ISCO (12 g column, 70-100% EtOAc in hexanes) gave 6-fluoro-2,3′-bipyridine (581 mg, 3.34 mmol, 99% yield) as a pale yellow crystalline solid. m/z (ESI, +ve ion) 175.1 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.20 (1H, d, J=1.6 Hz); 8.67 (1H, d, J=3.9 Hz); 8.34 (1H, d, J=8.0 Hz); 7.90 (1H, q, J=8.0Hz); 7.67 (1H, dd, J=7.5, 2.4 Hz); 7.42 (1H, dd, J=7.9, 4.8 Hz); 6.94 (1H, dd, J=8.0, 2.9 Hz).

Provenance & Evidence