Morpholine → N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-2-morpholin-4-yl-isonicotinamide

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 460 mg (1.06 mmol) 2-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-isonicotinamide, 693 mg (2.13 mmol) cesium carbonate and a few crystals of 2,6-di-tert-butyl-p-cresol in 2.78 ml (3.19 mmol) morpholine and 2 ml N-methylpyrrolidone in a thick-walled glass pressure tube fitted with a teflon cap was heated at 140° C. for 24 h. The reaction mixture was then cooled to room temperature and poured onto water. The mixture was extracted three times with ethyl acetate, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (2/98 methanol/dichloromethane) followed by trituration in ether afforded 136 mg (29%) N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-2-morpholin-4-yl-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 439 (M+H+, 100).

Provenance & Evidence