Triphenylphosphine → N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-vinyl-isonicotinamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 200 mg (0.45 mmol) 2-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide in 10 ml DMF were added 283 mg (0.89 mmol) vinyltri-n-butyltin, 38 mg (0.05 mmol) bis(triphenylphosphine)palladium(II) chloride, 70 mg (0.27 mmol) triphenylphosphine, 151 mg (3.57 mmol) lithium chloride and 10 mg (0.04 mmol) 2,6-di-tert-butyl-para-cresol. The mixture was heated at 100° C. for 48 h and then poured onto water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (hexane then 1/1 ethyl acetate/hexane) followed by trituration in hexane/dichloromethane afforded 100 mg (57%) N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-vinyl-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 396 (M+H+, 100).

Provenance & Evidence