Sodium Carbonate → 4-Chloro-2-(2,6-dichloro-4-vinyl-phenyl)-thiazolo[5,4-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-(2,6-dichloro-4-iodo-phenyl)-thiazolo[5,4-c]pyridine (0.30 g, 0.68 mmol), vinyl borane pinacol ester (0.105 g, 0.68 mmol), PdCl2(PPh3)2 (0.029 g, 0.04 mmol) and sodium carbonate (0.288 g, 2.70 mmol) in water (0.4 mL) and dioxane (4 mL) was degassed with nitrogen and heated at 100° C. for 2 hours. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-8% EtOAc in pentane to give the desired compound as an off-white solid (0.168 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 8.51 (d, J=5.6 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.53-7.45 (m, 2H), 6.69-6.62 (m, 1H), 5.91 (d, J=17.5 Hz, 1H), 5.52 (d, J=10.9 Hz, 1H).

Provenance & Evidence