C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:9]([O:11][CH3:12])=[O:10].[I:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)([CH3:30])[CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=1>CN(C=O)C>[I:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:9]([O:11][CH3:12])=[O:10])=[CH:35][CH:36]=2)([CH3:30])[CH:27]([CH3:28])[CH3:29])=[CH:24][CH:25]=1Cesium carbonate (1.5 equiv.) followed by methyl bromo(pyridin-2-yl)acetate (5i) (1 equiv.) are added to a stirred solution of 5b (1 equiv.) in DMF at room temperature. After completion of reaction, the reaction mixture is quenched with saturated aqueous ammonium chloride, poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound 5c.
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