Cesium carbonate → HCID 66742925, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round-bottomed flask, 6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)-N,N-dimethylnicotinamide (1.053 g, 3.42 mmol), 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (2.2 g, 4.45 mmol) and Cs2CO3 (3.34 g, 10.3 mmol) were combined with dioxane (20 ml) and water (2.00 ml) to give a dark brown suspension. The suspension was purged with argon and PdCl2(DPPF) (83.8 mg, 10.3 mmol) was added. The reaction mixture was heated to 85° C. and stirred for 3 h. Cooled to 25° C. and diluted with DCM. Na2SO4 was added and the mixture was filtered through celite. The filter cake was washed with DCM until clear and the brown filtrate was conc. in vacuo. The crude material was purified by flash chromatography (silica gel, 220 g, 0% to 5% MeOH in DCM). The product was isolated impure and repurified by flash chromatography (silica gel, 220 g, 100% EtOAc) to afford 1.1412 g (52%) of the title compound as a cream colored solid. (M+H)+=640 m/e.

Provenance & Evidence