Cesium fluoride → 4-Chloro-6-(4-isopropoxyphenyl)-6'-methoxy-2,2'-bipyridine

Participants

Reaction Steps

To a 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (50 mg, 0.18 mmol), 2-methoxy-6-(tributylstannyl)pyridine (701 mg, 0.178 mmol), CuI (9 mg, 0.05 mmol), CsF (82 mg, 0.54 mmol), and Pd(PPh3)4 (10 mg, 8.9 μmol). The vial was sealed with a septum screw-cap and then placed under N2 atmosphere. To the vial was added degassed DMF (1 mL). The vial was placed in a 80° C. heating block with stirring for 1 hour. The reaction mixture was allowed to cool to room temperature and was then directly purified via C18 chromatography (water:MeOH w/0.1% TFA) to afford 4-chloro-6-(4-isopropoxyphenyl)-6′-methoxy-2,2′-bipyridine as a dark solid (58 mg, 92%). 1H-NMR (500 MHz, CDCl3) 8.29 (d, J=1.7 Hz, 1H), 8.21 (dd, J=7.4, 0.5 Hz, 1H), 8.09-8.04 (m, 2H), 7.74 (t, J=7.8 Hz, 1H), 7.67 (d, J=1.7 Hz, 1H), 7.03-6.99 (m, 2H), 6.82 (dd, J=8.2, 0.5 Hz, 1H), 4.66 (spt, J=6.1 Hz, 1H), 4.08 (s, 3H), 1.40 (d, J=6.0 Hz, 6H); MS: MS m/z 355.2 (M++1).

Provenance & Evidence