Potassium Phosphate, Tribasic → [2-(2,6-Dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridin-4-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-bromo-thiazolo[5,4-c]pyridin-2-yl)-3,5-dichloro-benzonitrile (0.578 g, 1.50 mmol), tert-butyl carbamate (1.76 g, 15.0 mmol), Pd2(dba)3 (0.069 g, 0.075 mmol), XantPhos (0.087 g, 0.15 mmol) and tribasic potassium phosphate (0.635 g, 3.0 mmol) in toluene (10 mL) and water (1.5 mL) was degassed with argon then heated at 80° C. for 3 hours. The reaction mixture was filtered through Celite® and washed with EtOAc. The filtrate was washed with water then brine, dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (0-50% EtOAc in pentane) to give the desired compound as an off-white solid (0.48 g, 76% yield). 1H NMR (300 MHz, CDCl3): δ 8.35 (d, J=5.6 Hz, 1H), 7.79 (d, J=5.6 Hz, 1H), 7.75 (s, 2H), 1.56 (s, 9H).

Provenance & Evidence