Reaction SMILES: [Cl:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[C:16](I)[C:15]([N:19]3[CH2:22][CH:21]([CH2:23][OH:24])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1.[CH3:28][C:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[N:31](C2CCCCO2)[N:30]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[C:16]([C:32]3[NH:31][N:30]=[C:29]([CH3:28])[CH:33]=3)[C:15]([N:19]3[CH2:22][CH:21]([CH2:23][OH:24])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1
Reactant: Cc1cc(B2OC(C)(C)C(C)(C)O2)n(C2CCCCO2)n1
Reactant: O=C(Nc1ccc(OC(F)(F)Cl)cc1)c1cnc(N2CC(CO)C2)c(I)c1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])[O-]
Agent: O=P([O-])([O-])[O-]
Solvent: O=C(O)C(F)(F)F
Solvent: CCOC(C)=O
Solvent: Cc1ccccc1
Product: Cc1cc(-c2cc(C(=O)Nc3ccc(OC(F)(F)Cl)cc3)cnc2N2CC(CO)C2)[nH]n1
Temperature: 80 °C
Reaction time: 24 h

Procedure:
A mixture of N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)azetidin-1-yl)-5-iodonicotinamide (Stage 92.1, 175 mg, 0.343 mmol), 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (201 mg, 0.687 mmol), K3PO4 (219 mg, 1.030 mmol) and Pd(PPh3)4 (19.9 mg, 0.017 mmol) and toluene (2 mL) were added to a vial, which was sealed purged with argon stirred at 80° C. for 24 h. EtOAc (60 mL) was added and the solution was washed with aq. sat. NaHCO3 solution (20 mL) and brine (2×20 mL), dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give a residue which was purified by flash chromatography (RediSep® Silica gel column, 40 g, DCM/MeOH 95:5). The resulting intermediate was dissolved in DCM (2 mL), treated with TFA (0.554 mL, 7.19 mmol) and stirred at RT for 18 h. The RM was dissolved in EtOAc, washed with aq. sat. NaHCO3 solution and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by preparative HPLC (Condition 10). Fractions containing product were combined and the solvent was evaporated off under reduced pressure to give an MeCN aq. residue which was treated with Na2CO3 (1 g) and extracted with EtOAc. The combined organic phases were washed with water, dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The residue was dissolved in MeOH (3 mL), filtered through a SPE PL-Thiol cartridge (StratoSphere™, 500 mg 1.5 mmol), the cartridge was washed with MeOH and the solvent was evaporated off under reduced pressure to give a residue which was purified by preparative SFC (1: Column DEAP, from 20% to 25% in 11 min; 2: Column PFP, from 5% to 10% in 11 min) to give the title product as a white solid. HPLC (Condition 7) tR=5.675 min, UPLC-MS (Condition 8) tR=0.95 min, m/z=464.2 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 2.28 (br. s, 3H) 2.57-2.68 (m, 1H) 3.42-3.49 (m, 2H) 3.50-3.57 (m, 2H) 3.72-3.88 (m, 2H) 4.71 (br. s, 1H) 6.16 (s, 1H) 7.33 (d, J=8.53 Hz, 2H) 7.87 (d, J=8.91, 2H) 8.01 (s, 1H) 8.70 (br. s, 1H) 10.21 (s, 1H).