Water → 8-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline

Participants

Reaction Conditions

Reaction Steps

8-(Benzyloxy)-2-chloroquinoline (5.0 g, 18.5 mmol), 7-(2-methoxyethoxy)-imidazo[1,2-a]pyridine (3.56 g, 18.5 mmol), Pd(PPh3)4 (1.07 g, 0.927 mmol), K2CO3 (5.12 g, 37.1 mmol), and Pd(OAc)2 (0.208 g, 0.927 mmol) were added to dioxane (74.1 ml, 18.5 mmol) and water (0.735 ml, 40.8 mmol) and the reaction mixture was heated to 100° C. overnight under nitrogen. The reaction was diluted with DCM and 5 g of carbon were added followed by filtration. The slurry was concentrated and the filtrate was triturated with 1:1 EtOAc/MTBE (30 mL). The resulting solids were stirred for 5 hours and then filtered to isolate the desired product as a solid (5.4 g, 69% yield).

Provenance & Evidence