Dimethyl Sulfoxide → 4-Fluoro-6-(4-isopropoxyphenyl)-2,2'-bipyridine

Participants

Reaction Steps

To a 2 dram vial equipped with a stir bar and charged with 4-chloro-6-(4-isopropoxyphenyl)-2,2′-bipyridine (all material from step 1) was added cesium fluoride (200 mg, 1.32 mmol) and DMSO (0.7 mL). The vial was sealed with a septum cap and then placed in a 140° C. heating block with stirring for 18 h. The reaction mixture was allowed to cool to room temperature. The mixture was transfered to a 125 mL separatory funnel and was diluted with EtOAc (50 mL) and then twice washed with water:brine (25 mL:25 mL). The organic solution was dried over MgSO4; filtered; then concentrated in vacuo to afford an amber solid residue which was subjected to silica gel chromatography (hexane:EtOAc) to afford 4-fluoro-6-(4-isopropoxyphenyl)-2,2′-bipyridine as a colorless solid (16 mg, 29% over two steps). 1H-NMR (400 MHz, CDCl3) δ 8.72-8.67 (m, 1H), 8.62 (dt, J=7.8, 1.0 Hz, 1H), 8.10-8.05 (m, 3H), 7.86 (td, J=7.8, 1.8 Hz, 1H), 7.41 (dd, J=10.0, 2.3 Hz, 1H), 7.35 (ddd, J=7.5, 4.8, 1.3 Hz, 1H), 7.04-6.99 (m, 2H), 4.66 (spt, J=6.1 Hz, 1H), 1.40 (d, J=6.0 Hz, 6H); MS: MS m/z 309.2 (M++1).

Provenance & Evidence