C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:22]1[S:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].Br[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:38][C:39]([CH3:50])=[C:40]([CH2:42][CH2:43][N:44]3[CH2:48][CH2:47][CH2:46][C@H:45]3[CH3:49])[N:41]=2)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.O.C1(C)C=CC=CC=1>[CH3:50][C:39]1[O:38][C:37]([C:34]2[CH:35]=[CH:36][C:31]([C:25]3[S:26][C:22]([C:20]#[N:21])=[CH:23][CH:24]=3)=[CH:32][CH:33]=2)=[N:41][C:40]=1[CH2:42][CH2:43][N:44]1[CH2:48][CH2:47][CH2:46][C@H:45]1[CH3:49]Prepare using the method of Example 120 with palladium (II) acetate (0.008 g, 0.04 mmol), anhydrous toluene (5 mL), triphenylphosphine (0.038 g, 0.15 mmol), distilled water (1.5 mL), ethanol (1 mL), 5-cyanothiophene-2-boronic acid (0.21 g, 1.37 mmol), 2-(4-bromophenyl)-4-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole (See Intermediate 73) (0.32 g, 0.92 mmol) and potassium carbonate (0.38 g, 2.75 mmol). Additionally purify by trituration with ethyl acetate to give the title compound as a cream coloured solid (0.03 g): MS (m/e): 378(M+1).
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