1,10-Phenanthroline → HCID 68380034, compound

Participants

Reaction Conditions

Reaction Steps

Synthesis of 7-methoxy-2-(trifluoromethyl)-1,3-benzothiazole (C26). To a solution of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroethanethioamide (C25) (748 mg, 2.38 mmol) in 1,2-dimethoxyethane (11.9 mL) was added 1,10-phenanthroline (88.4 mg, 0.48 mmol), cesium carbonate (1.55 g, 4.76 mmol), and copper iodide (45.3 mg, 0.24 mmol). Nitrogen was bubbled through the reaction for 30 minutes and the reaction was heated to 80° C. for 48 hours. The mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% diethyl ether in hexanes) afforded the title compound as a colorless solid. Yield: 398 mg, 1.71 mmol, 72%. GCMS m/z 233 (M+). 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 6.97 (br d, J=7.9 Hz, 1H), 7.56 (dd, J=8.3, 8.0 Hz, 1H), 7.82 (dd, J=8.3, 0.6 Hz, 1H).

Provenance & Evidence