Reaction SMILES: [N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[C:15](=[O:22])[N:16]([CH3:21])[N:17]=[C:18](Cl)[CH:19]=3)=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C([O:26][CH2:27][C:28]1[C:33]([N:34]2[N:43]=[CH:42][C:41]3[C:36](=[C:37]([F:48])[CH:38]=[C:39]([C:44]([CH3:47])([CH3:46])[CH3:45])[CH:40]=3)[C:35]2=[O:49])=[CH:32][CH:31]=[CH:30][C:29]=1[B-](F)(F)F)(=O)C.[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH-].[Na+]>CO.O1CCOCC1.ClCCl.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[C:15](=[O:22])[N:16]([CH3:21])[N:17]=[C:18]([C:29]4[C:28]([CH2:27][OH:26])=[C:33]([N:34]5[N:43]=[CH:42][C:41]6[C:36](=[C:37]([F:48])[CH:38]=[C:39]([C:44]([CH3:45])([CH3:46])[CH3:47])[CH:40]=6)[C:35]5=[O:49])[CH:32]=[CH:31][CH:30]=4)[CH:19]=3)=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1
Reactant: Cn1nc(Cl)cc(Nc2ccc(C(=O)N3CCC3)cn2)c1=O
Reactant: CC(=O)OCc1c(-n2ncc3cc(C(C)(C)C)cc(F)c3c2=O)cccc1[B-](F)(F)F
Agent: [Pd]
Agent: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1
Agent: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
Solvent: ClCCl
Solvent: CO
Solvent: O
Product: Cn1nc(-c2cccc(-n3ncc4cc(C(C)(C)C)cc(F)c4c3=O)c2CO)cc(Nc2ccc(C(=O)N3CCC3)cn2)c1=O
Temperature: 100 °C
Reaction time: 1.67 h
Yield: 15 %

Procedure:
4-(5-(azetidine-1-carbonyl)pyridin-2-ylamino)-6-chloro-2-methylpyridazin-3(2H)-one (56 mg, 175 μmol, Eq: 1.00), potassium (2-(acetoxymethyl)-3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)phenyl)trifluoroborate (83.1 mg, 175 μmol, Eq: 1), x-phos (13.0 mg, 27.3 μmol, Eq: 0.156) and potassium phosphate tribasic (81.8 mg, 385 μmol, Eq: 2.2) were dissolved in a 10% aq. methanol solution (10 ml). The reaction was degassed. Finally bis(dibenzylideneacetone)palladium (9.06 mg, 15.8 μmol, Eq: 0.09) was added and the reaction mixture was stirred at 100° C. for 100 min. The reaction mixture was filtered and the filtercake was washed with methanol. The combined filtrate and washes were concentrated and extracted with ethyl acetate and water. The organic phase was separated, washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was dissolved in ethyl acetate. Hexane was added until precipitate was formed. The precipitate was filtered off to give crude product as a yellow solid. This crude product was purified by silica gel chromatography to give a yellow solid which was dissolved in dioxane. 1 M sodium hydroxide solution (263 μl, 263 μmol, Eq: 1.5) was added and the resulting reaction mixture was stirred over night at room temperature. The reaction mixture was treated again with 1 M sodium hydroxide solution (10 eq.) and heated to 40° C. for 4 hr. The reaction was diluted with dichlormethane and water and extracted with dichloromethane to give a crude solid after concentration. The crude product was purified by 12 g silica gel chromatography eluting with 0-10% methanol in ethyl acetate to afford 2-(3-{5-[5-(Azetidine-1-carbonyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yl}-2-hydroxymethyl-phenyl)-6-tert-butyl-8-fluoro-2H-phthalazin-1-one as a light yellow solid (16 mg). (M+H)+=610.1 m/e