Reaction SMILES: Cl[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C@@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[CH3:22])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.C([O:26][CH2:27][C:28]1[C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][CH:31]=[CH:30][C:29]=1[N:43]1[N:52]=[CH:51][C:50]2[C:45](=[C:46]([F:57])[CH:47]=[C:48]([C:53]([CH3:56])([CH3:55])[CH3:54])[CH:49]=2)[C:44]1=[O:58])(=O)C.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+]>C1COCC1.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].O.C(O)CCC>[C:53]([C:48]1[CH:49]=[C:50]2[C:45](=[C:46]([F:57])[CH:47]=1)[C:44](=[O:58])[N:43]([C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([C:2]3[CH:3]=[C:4]([NH:10][C:11]4[CH:16]=[CH:15][C:14]([C@@H:17]5[CH2:21][CH2:20][CH2:19][N:18]5[CH3:22])=[CH:13][N:12]=4)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=3)[C:28]=1[CH2:27][OH:26])[N:52]=[CH:51]2)([CH3:56])([CH3:54])[CH3:55]
Reactant: CC(=O)OCc1c(B2OC(C)(C)C(C)(C)O2)cccc1-n1ncc2cc(C(C)(C)C)cc(F)c2c1=O
Reactant: CN1CCC[C@H]1c1ccc(Nc2cc(Cl)nn(C)c2=O)nc1
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: C1CCOC1
Solvent: O
Solvent: CCCCO
Product: CN1CCC[C@H]1c1ccc(Nc2cc(-c3cccc(-n4ncc5cc(C(C)(C)C)cc(F)c5c4=O)c3CO)nn(C)c2=O)nc1
Temperature: 110 °C
Reaction time: 25 h
Yield: 24 %

Procedure:
In a 50 mL RB flask, (S)-6-chloro-2-methyl-4-(5-(1-methylpyrrolidin-2-yl)pyridin-2-ylamino)pyridazin-3(2H)-one (125 mg, 0.39 mmol) and 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 (331 mg, 468 μmol) were combined with BuOH (4 ml) to give a orange solution. 1 mL of water was added. Purged with argon. X-PHOS (18.6 mg, 39.0 μmol) and potassium phosphate tribasic (166 mg, 780 μmol, were added. Argon was bubbled through for 10 min. Bis(dibenzylideneacetone)-palladium (0) (11.2 mg, 19.5 μmol) was added. The resultant reaction mixture was purged with argon and warmed in a oil bath at 110° C. for 1.5 hours. Two main products were observed by LCMS, acetylated and deacetylated product. The reaction was allowed to cool to RT overnight and then was concentrated to small volume. The reaction mixture was poured into 75 mL H2O and extracted with EtOAc (3×75 mL). The organic layers were washed with brine and dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 1% to 5% MeOH in DCM) to afford 2 peaks. The two peaks were combined and concentrated to give 238 mg of a 1:1 mixture of acetylated and deacetylated product. This mixture was taken up in 15 mL THF and treated with 2 mL of 1N NaOH. The reaction mixture was heated to 60° C. and stirred for 25 h. The reaction was almost complete by tlc. The reaction mixture was poured into 100 mL H2O and extracted with EtOAc (2×50 mL) and DCM (1×). No product remained in the aqueous phase. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 1% to 5% MeOH in DCM) two times, followed by trituration with ethyl acetate/hexanes to afford 57 mg pure product. (M+H)+=610 m/e.