1,10-Phenanthroline → N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 760 mg (1.53 mmol) 1-benzoyl-3-[3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-yl]-thiourea, 29 mg (0.15 mmol) copper(I) iodide, 55 mg (0.31 mmol) 1,10-phenanthroline and 1.00 g (3.06 mmol) cesium carbonate in 4 ml toluene was heated at 130° C. for 10 min in a microwave oven. The resulting mixture was then cooled to room temperature and concentrated in vacuo. The residue was resuspended in methanol, the mixture filtered, and the filtrate concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 314 mg (56%) N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide as a white solid. ES-MS m/e (%): 370 (M+H+, 100).

Provenance & Evidence