Potassium Carbonate → HCID 86687527, compound

Participants

Reaction Steps

A microwave vial charged with 4,7-dichlorocinnoline hydrochloride (HDH Pharma, Morrisville, N.C.) (0.400 g, 1.7 mmol), 2-methoxy-4-(trifluoromethyl)phenylboronic acid (Combi-Blocks, San Diego, Calif.) (0.513 g, 1.7 mmol), potassium carbonate (1.172 g, 8.49 mmol), dioxane (6.36 ml) and water (2.1 ml); the system was purged with argon prior to the addition of Pd(PPh3)4 (0.196 g, 0.168 mmol). The mixture was irradiated for 30 min at 100° C. The organic layer was decanted and the aqueous phase was rinsed once with EtOAc. The combined organics were dried under reduced pressure and purified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0 to 35%, 10% DCM throughout) providing 7-chloro-4-(2-methoxy-4-(trifluoromethyl)phenyl)cinnoline (0.212 g, 0.626 mmol, 36.8% yield) as a light yellow solid. m/z (ESI) 339.2 (M+H)+.

Provenance & Evidence