[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([O:8][CH2:9][C:10]2[C:11]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[N:12][O:13][C:14]=2[CH:15]2[CH2:17][CH2:16]2)[CH2:3][CH2:2]1.Br[C:27]1[CH:39]=[CH:38][C:30]2[C:31]([C:34]([O:36][CH3:37])=[O:35])=[N:32][S:33][C:29]=2[CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C(C)=CC=CC=1>[CH:15]1([C:14]2[O:13][N:12]=[C:11]([C:18]3[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][C:23]=3[Cl:24])[C:10]=2[CH2:9][O:8][CH:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:27]3[CH:39]=[CH:38][C:30]4[C:31]([C:34]([O:36][CH3:37])=[O:35])=[N:32][S:33][C:29]=4[CH:28]=3)[CH2:2][CH2:3]2)[CH2:16][CH2:17]1To an oven dried flask purged with argon, add 4-((azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol (0.51 g, 1.34 mmol), methyl 6-bromobenzo[d]isothiazole-3-carboxylate (0.30 g, 1.10 mmol), cesium carbonate (0.51 g, 1.56 mmol), X-Phos (0.04 g, 0.084 mmol), xylene (10 ml) and Pd2(dba)3 (0.025 g, 0.028 mmol). Purge the mixture with argon and heat to 130° C. until the starting materials are consumed as confirmed by TLC. Cool the reaction mixture to room temperature, filter through celite and concentrate in vacuo. The crude product is purified by flash chromatography on silica gel eluting with 6:4 hexane/ethyl acetate to give 0.30 g (47.0%) of the title compound as an off white solid. ES/MS m/z 571.11 (M+1).
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