[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[NH:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:7]=[CH:6][N:5]=1.[CH2:26](Br)[CH:27]=[CH2:28].[Cl-].[NH4+]>CN(C)C=O>[CH2:28]([N:18]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:10]1[C:8]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:3])[CH:9]=1)[CH:27]=[CH2:26]Sodium hydride (120 mg, 3 mmole 60% in oil) is added to a solution of 323.5 mg (1 mmole) of 2-(2-Chloro-pyridin-4-yl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine in 8 mL of dimethylformamide at room temperature. After 30 min. at room temperature, 1.2 g of allyl bromide (10 mmoles) is added to the reaction mixture. After 1 hour at room temperature, the reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. After concentration the solid residue is purified by chromatography on silica gel (ethyl acetate/hexane 1/1) to give 270 mg of 1-Allyl-2-(2-chloro-pyridin-4-yl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine as white solid.
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