1,10-Phenanthroline → HCID 59455182, compound

Participants

Reaction Conditions

Reaction Steps

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (200 mg, 1 mmol) was dissolved in toluene (8-10 mL). Copper sulfate (50 mg, 0.2 mmol), 1,10-phenanthroline (72 mg, 0.4 mmol), potassium phosphate (425 mg, 2 mmol) and 1-(bromoethynyl)-4-chlorobenzene (237 mg, 1.1 mmol) was added and the mixture flushed with nitrogen. The reaction mixture was heated at 80° C. overnight (16 h). Product was detected by LCMS. The reaction mixture was filtered through Celite, washed with DCM. The combined organic layer was concentrated under vacuum to obtain product, which was purified by column chromatography (Silica gel-60-80% EtOAc in hexane) to obtain product (38 mg) as a yellow solid. 1H NMR (CDCl3, TFA salt) δ (ppm): 7.52-7.40 (m, 3H), 7.36-7.30 (m, 2H), 7.20 (s, 1H), 7.12-7.09 (d, 1H), 3.77 (s, 2H), 3.06-2.94 (m, 4H), 2.62 (s, 3H), 2.42 (s, 3H).

Provenance & Evidence