2-Bromopyridine → HCID 21462565, compound

Participants

Reaction Conditions

Reaction Steps

2-(2,2-bis(Difluoromethyl)-6-phenylsulfonyl-3,4-dihydro-2H-1,4-benzoxazine-4-yl)pyridine. A mixture of the product of step e. (1 g), potassium carbonate (0.41 g), copper bronze (0125 g,), and 2-bromopyridine (4.3 g) was stirred and heated at 200° C. for 18 hours. The cooled, dark mixture was stirred with water and ethyl acetate:dichloromethane. The mixture was filtered through diatomaceous earth, and the lower organic layer was separated. The organic phase was washed (water), dried, and evaporated. Chromatography, eluting ethyl acetate:hexane (gradient 40% to 60%) gave the pyridine as a pale yellow gum (0.29 g); NMR: 4.31 (s,2), 6.49 (t,2), 7.06 (t,1), 7.21 (d,1), 7.33 (d,1), 7.53 (d,1), 7.60 to 7.70 (m,3), 7.79 (t,1), 7.92 (d,2), 7.94 (s,1), 8.36 (d,1); MS: m/z=453(M+1).

Provenance & Evidence