[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.Br[CH2:27][CH2:28][F:29].[Cl-].[NH4+]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[N:18]([CH2:27][CH2:28][F:29])[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]=1Sodium hydride (371 mg, 9.3 mmoles 60% in oil) is added to a solution of 1 g (3.1 mmoles) of 2-(2-Chloro-pyridin-4-yl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine (prepared following the procedure for example 6) in 20 mL of dimethylformamide at room temperature. After 30 min. at room temperature, 2.75 g of 1-bromo-2-fluoro-ethane (21.6 mmoles) is added to the reaction mixture. After 10 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 720 mg of 2-(2-Chloro-pyridin-4-yl)-1-(2-fluoro-ethyl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine as white solid.
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