[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2].Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]23[CH2:41][CH2:40][C:37]([CH2:42][C:43]([O:45][CH3:46])=[O:44])([CH2:38][CH2:39]2)[O:36][CH2:35]3)=[CH:30][CH:29]=1.O.[F-].[Cs+]>O1CCOCC1.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:28]3[CH:29]=[CH:30][C:31]([C:34]45[CH2:39][CH2:38][C:37]([CH2:42][C:43]([O:45][CH3:46])=[O:44])([CH2:40][CH2:41]4)[O:36][CH2:35]5)=[CH:32][CH:33]=3)=[CH:16][CH:17]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2]To a solution of 2-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide (200 mg, 0.561 mmol) and methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (190 mg, 0.561 mmol) in dioxane (3 ml) was added H2O (0.33 ml). CsF (256 mg, 1.684 mmol) and Pd(amphos)Cl2 (39.8 mg, 0.056 mmol) were then added and the mixture was degassed before being heated at 90° C. for overnight. The reaction mixture was then cooled to room temperature and directly purified by column chromatography to afford the title compound as white solid after drying (159 mg, 58% yield). LC/MS, ESI-MS(+): 489.0, RT: 1.40 (Condition E).
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