Potassium Phosphate, Tribasic → [3,5-Dichloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-phenyl]-carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine (0.40 g, 0.905 mmol), carbamic acid tert-butyl ester (0.159 g, 1.36 mmol), XantPhos (0.053 g, 0.091 mmol) and K3PO4 (0.384 g, 1.81 mmol) in toluene (9 mL) and water (1.5 mL), was degassed with a stream of argon. Pd2(dba)3 (0.041 g, 0.045 mmol) was then added and the reaction mixture was heated at 85° C. for 2 hours using microwave irradiation and then thermally at 100° C. for 18 hours. After cooling to room temperature, the crude residue was partitioned between water and EtOAc. The aqueous phase was further extracted with EtOAc (×2) and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-10% EtOAc in cyclohexane to afford the title compound as an off-white solid (0.352 g, 90% yield). LCMS (Method D): RT=4.68 min, m/z: 430 [M+H+].

Provenance & Evidence