Potassium Phosphate, Tribasic → 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(5-(5-(1-ethylpiperidin-4-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)benzyl acetate

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In a 50 mL test tube, 6-chloro-4-(5-(1-ethylpiperidin-4-yl)pyridin-2-ylamino)-2-methylpyridazin-3(2H)-one (121 mg, 348 μmol, Eq: 1.00) and potassium (2-(acetoxymethyl)-3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)phenyl)trifluoroborate (165 mg, 348 μmol, Eq: 1.00) were combined with BuOH (4 ml) to give a orange solution. Water (1.00 ml) was added. X-PHOS (16.6 mg, 34.8 μmol, Eq: 0.1) and potassium phosphate tribasic (148 mg, 696 μmol, Eq: 2) were added. Bis(dibenzylideneacetone)palladium (10.0 mg, 17.4 μmol, Eq: 0.05) was added. The reaction mixture was purged with argon. The mixture was heated in a oil bath at 100° C. for 1.5 hours, then cooled to room temperature. The reaction mixture was poured into 75 mL H2O and extracted with twice with EtOAc. The organic layers were combined and dried over Na2SO4. Concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 50% to 100% (60:10:1 DCM:MeOH:NH4OH)/DCM gradient) to give a solid. The solid was triturated with Et2O to give 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(5-(5-(1-ethylpiperidin-4-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)benzyl acetate (147 mg, 62%). LC/MS-ESI observed [M+H]+ 680.

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