1,10-Phenanthroline → HCID 86711726, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Compound 10 (20.3 g, 36.7 mmol), CuI (0.700 g, 3.67 mmol), Cs2CO3 (23.9 g, 73.5 mmol), 1,10-phenanthroline (1.32 g, 7.35 mmol) and 1,4-dioxane (300 mL) was degassed with Ar and then maintained at about 120° C. overnight. Upon confirming consumption of the starting material by TLC (SiO2, 4:1 hexanes-ethyl acetate), the reaction was cooled to RT and diluted with EtOAc (ca. 300 mL) and H2O (ca. 400 mL). The resulting suspension was then filtered and the filtrant washed copiously with H2O and CH3OH to provide Compound 11 (12.7 g, 88%) as an off-white solid: confirmed by LCMS (APCI): calculated for C20H11BrN2O2 (M+): 391; Found: 391.

Provenance & Evidence