Potassium Carbonate → HCID 86687627, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask was charged with perfluorophenyl 1-chloroisoquinoline-6-sulfonate (see EXAMPLE 73, Step 1, 518.97 mg, 1.267 mmol), (4-chloro-2-methylphenyl)boronic acid (324 mg, 1.900 mmol), potassium carbonate (525 mg, 3.80 mmol), and Pd(PPh3)4 (146 mg, 0.127 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (4750 μl) and water (1583 μl) were added. The flask was sealed and heated in a 50° C. heating bath overnight. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 0-30% EtOAc/Heptane) to give perfluorophenyl 1-(4-chloro-2-methylphenyl)isoquinoline-6-sulfonate (249 mg, 0.498 mmol, 39.3% yield) as a clear oil. m/z (ESI) 500.0 (M+H)+.

Provenance & Evidence