2-Methoxy-4-(tributylstannyl)thiazole → 1-[5-[2-(Ethylcarbamoylamino)-7-(2-methoxythiazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (150 mg, 0.274 mmol), tetrakis(triphenylphosphine)palladium (16 mg, 0.0138 mmol) and 2-methoxy-4-(tributylstannyl)thiazole (0.33 mL, 0.822 mmol) in anhydrous DMF (3.0 mL) was purged with N2 for 20 min. The reaction vessel was sealed and heated at 110° C. for 10 h. After cooling to rt, the mixture was diluted with water (50 mL) and extracted with EtOAc (3×20 mL) which was washed with brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash silica chromatography eluting with 0 to 100% EtOAc in iso-hexane to give 99 mg of the desired product as an off white gummy solid.

Provenance & Evidence