1,10-Phenanthroline → 2-Chloro-4-(pyridin-2-ylmethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

Pyridin-2-ylmethanol (3.00 g, 27.5 mmol), 2-chloro-4-iodopyridine (6.0 g, 25 mmol), cesium carbonate (10.6 g, 32.5 mmol), CuI (0.95 g, 5.0 mmol) and 1,10-phenanthroline (0.90 g, 5.0 mmol) were stirred in toluene (15 mL) and purged with a nitrogen stream for 10 minutes. The mixture was heated to 105° C. for 16 h, allowed cool and filtered through a silica plug eluting with ethyl acetate. The filtrate was concentrated, and the residue was purified by column chromatography (80 g ISCO column column eluting with ethyl acetate/hexanes; gradient 100% hexanes to 100% ethyl acetate) to provide the title compound (4.1 g, 74%) as a white solid: ESI MS m/z 221 [M+H]+.

Provenance & Evidence