Cesium carbonate → HCID 178480728, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (4Z)-4-({[2-fluoro-6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino}methylene)-6-iodoisoquinoline-1,3(2H,4H)-dione (0.10 g, 0.20 mmol), 3-furanboronic acid (55 mg, 0.50 mmol), tris(dibenzylideneacetone)dipalladium(0) (27 mg, 0.03 mmol) and cesium carbonate (0.13 g) in N,N-dimethylformamide (2 mL) is heated in a 120° C. oil bath for 10 minutes. Tri-tert-butylphosphine (20 mg/mL solution in N,N-dimethylformamide, 0.50 mL, 10 mg, 0.05 mmol) is added, and the mixture continued to stir in the oil bath for one hour. After cooling to room temperature, the reaction mixture is diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer is concentrated under reduced pressure and purified via reverse phase HPLC to provide (4Z)-4-({[2-fluoro-6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino}methylene)-6-(3-furyl)isoquinoline-1,3(2H,4H)-dione.3 trifluoroacetic acid salt (53 mg, 34%).

Provenance & Evidence