Dimethylformamide → Tert-butyl 5-(phthalazin-6-yl)thiazol-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 6-bromophthalazine (1.0 g, 5 mmol), tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (4.0 g, 7 mmol), DMF (4 mL), cesium fluoride (1.0 g, 10 mmol), copper(I) iodide (0.2 g, 1.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.2 mmol). The reaction mixture was stirred and heated at 100° C. overnight. The mixture was diluted with DCM (20 mL) and water (5 mL) and filtered through Celite. The organic solution was evaporated under reduced pressure, and the residue was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 10% MeOH in DCM to provide the title compound (1.19 g, 76%). LCMS (M+H+) 329.3 calc. for C16H16N4O2S 329.3; 1H NMR (400 MHz, CDCl3) δ ppm 9.50 (s, J=13.69 Hz 1H), 9.46 (s, 1H), 8.01 (d, J=1.37, Hz 1H), 7.92 (d, J=8.41 Hz, 1H), 7.81 (s, 1H), 7.58 (s, 1H) 1.40 (s, 9H).

Provenance & Evidence