Potassium Phosphate, Tribasic → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

Participants

Reaction Steps

A degassed solution of 3-(nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.74 g, 1.5 mmol), 2fluoro -4-methylsulfanyl-phenylamine (0.12 g, 0.76 mmol), Pd2 dba3 (0.035 g, 0.038 mmol), Xantphos (0.044 g, 0.076 mmol) and K3PO4 (0.32 g, 1.5 mmol) in toluene (10 ml) was heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature then filtered through a pad of Hyflo washing with ethyl acetate. The filtrate was concentrated in vacuo and the resultant residue subjected to flash chromatography (Si-SPE, gradient 0-10% ethyl acetate in dichloromethane) to provide the title compound as a yellow solid (0.16 g, 57%). LCMS (method B): RT=3.84 min, M+H+ 363.

Provenance & Evidence