Reaction SMILES: Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:29][C:30]1[S:31][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:33][N:34]=1.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.CO.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.O.O1CCOCC1>[OH:28][CH2:27][C@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:32]3[S:31][C:30]([CH3:29])=[N:34][CH:33]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1
Reactant: Cc1ncc(B2OC(C)(C)C(C)(C)O2)s1
Reactant: O=C(Nc1ccc(OC(F)(F)F)cc1)c1cnc(N2CC[C@H](CO)C2)c(Br)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: [Na+]
Solvent: C1COCCO1
Solvent: O
Solvent: CCOC(C)=O
Product: Cc1ncc(-c2cc(C(=O)Nc3ccc(OC(F)(F)F)cc3)cnc2N2CC[C@H](CO)C2)s1
Temperature: 80 °C
Reaction time: 18 h

Procedure:
(S)-5-Bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 16.1, 92 mg, 0.2 mmol), 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (90 mg, 0.4 mmol), Na2CO3 (53 mg, 0.5 mmol), dioxane (1 mL) and water (0.6 mL). were added to a MW vial, which was sealed and evacuated/purged with argon. Pd(Ph3P)4 (11.56 mg, 0.01 mmol) was added and the RM was stirred at 80° C. for 18 h. The RM was dissolved in EtOAc, washed with brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give a residue. The residue, 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (90 mg, 0.4 mmol), Na2CO3 (53 mg, 0.5 mmol), dioxane (1 mL) and water (0.6 mL) added to an MW vial which was sealed and evacuated/purged with argon. Pd(Ph3P)4 (11.56 mg, 0.01 mmol) was added and the RM was stirred at 80° C. for 18 h. After cooling the RM was dissolved in EtOAc, washed with brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give a crude product was purified by flash chromatography (RediSep® Silica gel column, DCM/MeOH from 2% to 5% MeOH) followed by reverse phase chromatography (MPLC, Lichroprep® 15-25 μm column, water+0.1% formic acid/MeCN+0.1% formic acid, gradient 10% to 40% MeCN+0.1% formic acid). The fractions containing pure product were combined, treated with excess aqueous NaHCO3 and extracted with EtOAc. The combined extracts were dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give a residue which was dissolved in MeOH and the solvent was evaporated off under reduced pressure to afford the title compound as an off-white amorphous solid. HPLC (Condition 4) tR=5.1 min, UPLC-MS (Condition 6) m/z=479.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.59 (m, J=7.40 Hz, 1H) 1.85 (m, J=6.30 Hz, 1H) 2.15-2.31 (m, 1H) 2.68 (s, 3H) 3.03-3.19 (m, 1H) 3.21-3.40 (m, 5H) 4.63 (t, J=5.28 Hz, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.60 (s, 1H) 7.83 (d, J=8.99 Hz, 2H) 8.03 (d, J=2.35 Hz, 1H) 8.73 (m, J=1.00 Hz, 1H) 10.17 (s, 1H).