Cesium carbonate → HCID 25109751, compound

Participants

Reaction Steps

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (50 mg, 0.164 mmol) and cesium carbonate (160 mg, 0.492 mmol) were suspended in DMF (1 μL) at room temperature under N2. To this was added 2-bromo-1-pyridin-3-ylethanone (48.3 mg, 0.172 mmol) as a solid. The resulting mixture was stirred under N2 for 16 hours. The reaction mixture was then diluted with water (2 mL) and extracted with EtOAc (2×15 mL). The combined organic fractions were washed with water (3×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. The product was lyophilized to afford the title compound. 1H NMR (DMSO-d6) δ 9.30 (s, 1H), 8.90 (m, 1H), 8.44 (d, J=7.8 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 7.85 (m, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.68 (m, 1H), 7.60 (m, 1H), 7.57 (m, 1H), 6.68 (s, 2H). HRMS (M+1)=424.0395

Provenance & Evidence