Reaction SMILES: [C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19](Cl)[C:18]=1[CH2:24][OH:25])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[CH3:26][N:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([N:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)=[CH:45][N:44]=2)[C:28]1=[O:56].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C([O-])([O-])=O.[K+].[K+]>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].CC(O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:31]3[CH:30]=[C:29]([NH:42][C:43]4[CH:48]=[CH:47][C:46]([N:49]5[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH2:54]5)=[CH:45][N:44]=4)[C:28](=[O:56])[N:27]([CH3:26])[CH:32]=3)[C:18]=1[CH2:24][OH:25])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]
Reactant: CN1CCN(c2ccc(Nc3cc(B4OC(C)(C)C(C)(C)O4)cn(C)c3=O)nc2)CC1
Reactant: CC(C)(C)c1cc(F)c2c(=O)n(-c3cccc(Cl)c3CO)ncc2c1
Agent: [Pd]
Agent: C1CCC(P(C2CCCCC2)C2CCCCC2)CC1
Agent: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
Solvent: CC(C)O
Product: CN1CCN(c2ccc(Nc3cc(-c4cccc(-n5ncc6cc(C(C)(C)C)cc(F)c6c5=O)c4CO)cn(C)c3=O)nc2)CC1
Temperature: 88 °C
Reaction time: 1.5 h

Procedure:
To a 2 L reactor were added 6-tert-butyl-2-(3-chloro-2-hydroxymethyl-phenyl)-8-fluoro-2H-phthalazin-1-one (64 g, 0.18 mol), 1-methyl-3-[5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one (90.5 g, 0.21 mol), PCy3 (3.0 g, 10.7 mmol), Pd(dba)2 (3.1 g, 5.4 mmol) and K2CO3 (49 g, 0.36 mol) in order. The reactor was evacuated and backfilled with Nitrogen. This sequence was repeated three times. Then, 20% aqueous 1,4-dioxane was added to the reaction mixture. The resulting mixture was heated to 88° C. for gentle reflux and stirred for 1.5 hr under Nitrogen atmosphere. After 2 hr reaction time, bath temperature was down to 80° C., and 1.3 L of IPA was added to the reaction mixture slowly with keeping the temperature above 70° C. The material started to come out, and the slurry was allowed to cool down to room temperature with stirring. Solid material was collected with filtration, and washed with IPA, water and then IPA again. The crude solid was dissolved with DCM (780 mL) and MeOH (100 ml) again. To the solution was added trithiocyanuric acid trisodium salt, 15% aqueous solution (490 ml), then the resulting mixture was stirred vigorously at ambient temperature for 2 hr. After adding Activated carbon (9.7 g) and Diatomaceous Earth (9.7 g) to the solution, the resulting mixture was stirred additional 2 hr at room temperature, then filtered through a short pad of Diatomaceous Earth. DCM layer was collected by phase separation, and the aqueous layer was extracted with additional DCM (490 ml). The combined organics were diluted with HCl, 1.0 M solution (780 mL), then DCM was removed by rotary evaporator under vacuum. During the evaporization, IPA was added to the mixture to chase DCM completely. The aqueous acidic solution was titrated with NH4OH, 30% solution to get the material out dropwise at ambient temperature. The desired product started to crystallize out from IPA/water, and the crystal material was collected by filtration, washed with water and IPA. The filter cake was dried under vacuum oven at 60° C. to afford 92.4 g of the title compound (83.5% isolated yield) as a yellow solid. MS (ESI) 624 (M+H)+. 1H NMR (400 MHz, DMSO-d6) d ppm 1.38 (s, 9H) 2.20 (s, 3H) 2.39-2.46 (m, 4H) 2.99-3.07 (m, 4H) 3.58 (s, 3H) 4.30-4.39 (m, 2H) 4.58 (t, J=5.31 Hz, 1H) 7.21 (d, J=9.09 Hz, 1H) 7.29 (d, J=2.53 Hz, 1H) 7.35 (dd, J=9.09, 3.03 Hz, 1H) 7.37-7.43 (m, 2H) 7.49 (d, J=7.58 Hz, 1H) 7.74 (dd, J=13.14, 2.02 Hz, 1H) 7.87 (dd, J=4.04, 2.53 Hz, 2H) 8.36 (s, 1H) 8.50 (d, J=2.53 Hz, 1H) 8.53 (d, J=3.5 Hz, 1H).