Potassium Carbonate → HCID 53380866, compound

Participants

Reaction Conditions

Reaction Steps

2-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-4-hydroxybenzonitrile (12-2) (300 mg, 0.77 mmol, 1 eq) was dissolved in acetonitrile (2.5 mL) and 6-chloropyridine-2-carbonitrile (212 mg, 1.5 mmol, 2 eq) and potassium carbonate (424 mg, 3.1 mmol, 4 eq) were added. The resulting mixture was heated in the microwave at 140° C. for 1.5 hours. The mixture was filtered washing with acetonitrile. The crude mixture was purified by reverse phase chromatography (Waters Sunfire MSC18, 10-100% acetonitrile in water with 0.1% TFA modifier) to afford 6-(4-cyano-3-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}phenoxy)pyridine-2-carbonitrile (12-3) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.90 (t, J=8.0 Hz, 1 H); 7.82 (d, J=8.4 Hz, 1 H); 7.50 (d, J=7.2 Hz, 1H); 7.34 (s, 1H); 7.29 (t, J=10.4 Hz, 1 H); 6.99 (s, 2 H); 6.92 (d, J=8.0 Hz, 2H), 3.92 (d, J=6.8 Hz, 2H); 3.36 (s, 3 H); 2.14 (m, 1 H); 1.65 (m, 1 H); 1.41 (m, 1 H). HRMS m/z (M+H) 494.1097 found, 494.1093 required.

Provenance & Evidence