2-Bromopyridine → HCID 21099415, compound

Participants

Reaction Steps

Butyllithium (1.6M in hexanes, 0.3 mL, 0.48 mmol) was added to a rapidly stirred solution of 2-bromopyridine (44 μL, 0.46 mmol) in tetrahydrofuran (1.2 mL) at −78° C. After 45 minutes, zinc chloride (1.0M in diethyl ether, 1.38 mL, 1.38 mmol) was added. The mixture was warmed to room temperature, tetrakis(triphenylphosphine)palladium(0) (27 mg) and 1-((E)-2-{4-[(3-bromophenyl)sulfonyl]phenyl}vinyl)-2,4-difluorobenzene (Example 109; 100 mg, 0.23 mmol) were added and the reaction heated to reflux overnight. The cooled reaction mixture was partitioned between ethyl acetate and 10% aqueous ethylenediaminetetraacetic acid, disodium salt. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 35% ethyl acetate/isohexane, to yield the title compound as a white solid (10 mg, 10%). δH (400 MHz, CDCl3): 8.69 (1H, d, J=4.7 Hz), 8.56 (1H, t, J=1.7 Hz), 8.23 (1H, d, J=7.8 Hz), 7.98-7.94 (3H, m), 7.80-7.74 (2H, m), 7.62-7.50 (4H, m), 7.29-7.23 (2H, m), 7.07 (1H, d, J=16.5 Hz), 6.90-6.80 (2H, m). m/z (ES+) 434 [MH+].

Provenance & Evidence