[H-].[Na+].[N:3]1([CH2:12][C:13]#[N:14])[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1.Br[CH2:16][CH2:17][CH2:18][CH2:19]Br.CCOCC>CS(C)=O.CCCCCC.C(OCC)(=O)C>[N:3]1([C:12]2([C:13]#[N:14])[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1
To a suspension of sodium hydride (60%) (8.6 g, 215.79 mmol) in dimethyl sulfoxide (90 mL) was added dropwise a mixture of pyrrolo[2,3-b]pyridin-1-yl-acetonitrile (392) (15.4 g, 98.09 mmol) and 1,4-dibromo-butane (31.7 g, 147.13 mmol) dissolved in dimethyl sulfoxide: ether (180 mL, 1:1) at 0° C. and the reaction mixture was stirred for 30 min at same temperature, then stirred at room temperature for 24 h. (TLC, 40% ethyl acetate in hexane, Rf=0.6). After completion of the reaction, the reaction mixture was quenched with 1N HCl (100 mL). Water (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The separated organic part was washed with water (3×100 mL) and brine (2×100 mL) and dried and concentrated to get a crude product which was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to afford 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonitrile (393) (18 g, 87%) as a light yellow crystalline solid.
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