Reaction SMILES: Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][O:12][C:11]2[CH:15]=[C:16]([S:19]([N:22]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:23]3[S:24][CH:25]=[CH:26][N:27]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:10]1=2.B1([C:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH:47]=2)OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.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>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([N:9]2[CH2:14][CH2:13][O:12][C:11]3[CH:15]=[C:16]([S:19](=[O:21])(=[O:20])[N:22]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)[C:23]4[S:24][CH:25]=[CH:26][N:27]=4)[CH:17]=[CH:18][C:10]2=3)=[C:2]([C:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH:47]=2)[CH:7]=1
Reactant: CC(C)(C)OC(=O)N1CC=C(B2OC(C)(C)C(C)(C)O2)CC1
Reactant: COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(c2)OCCN3c2ccc(Cl)cc2Br)cc1
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: [K+]
Solvent: ClCCl
Solvent: C1COCCO1
Solvent: O
Product: COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(c2)OCCN3c2ccc(Cl)cc2C2=CCN(C(=O)OC(C)(C)C)CC2)cc1
Temperature: 100 °C

Procedure:
A microwave vial was charged with 4-(2-bromo-4-chlorophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.576 g, 0.949 mmol), (N-tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (0.293 g, 0.949 mmol), tetrakis(triphenylphosphine)palladium(0) (0.110 g, 0.095 mmol), and K2CO3 (0.656 g, 4.75 mmol). The solids were diluted with dioxane (6.33 mL) and water (3.16 mL), and the reaction was heated under microwave irradiation at 100° C. for 30 minutes. The reaction was diluted with water and DCM, and the layers separated. The aqueous was washed once more with DCM, and the organics were combined and dried using a phase separator to yield material. The material was then further purified via silica gel MPLC eluting with 0 to 100% ethyl acetate in heptane to yield tert-butyl 4-(5-chloro-2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3 H)-yl)phenyl)-5,6-dihydropyridine-1(2 H)-carboxylate as a red oil. A portion of material (117 mg) was diluted with 1.00 mL of DCM, and TFA (1.00 mL) and the reaction was stirred at RT for 5 minutes. The material was concentrated under a vacuum and purified via HPLC to yield 4-(4-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide 2,2,2-trifluoroacetate (0.073 g, 0.121 mmol, 12.76% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.30-2.43 (m, 1 H) 2.54 (m, J=0.60 Hz, 1 H) 3.15-3.23 (m, 2 H) 3.52 (m, J=3.30 Hz, 2 H) 3.63-3.70 (m, 2 H) 4.25-4.32 (m, 2 H) 5.82 (br. s., 1 H) 6.33 (d, J=8.31 Hz, 1 H) 6.79 (d, J=4.50 Hz, 1 H) 7.09-7.15 (m, 2 H) 7.23 (d, J=4.60 Hz, 1 H) 7.36-7.41 (m, 2 H) 7.45-7.50 (m, 1 H) 8.79 (br. s., 2 H) 12.55 (br. s., 1H). m/z (ESI) 489.0 (M+H)+.