[N:1]1([C:10]2([CH2:15][C:16]([NH2:18])=O)[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.N1C(Cl)=NC(Cl)=NC=1Cl.C(OCC)(=O)C.O>CN(C)C=O.CCCCCC>[N:1]1([C:10]2([CH2:15][C:16]#[N:18])[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1
To a stirred solution of 2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamide (398) (1.6 g, 6.58 mmol) in dimethylformamide (25 mL) was added cyanuric chloride (728 mg, 3.95 mmol) at room temperature. The reaction mixture was stirred for 30 min at room temperature (TLC, 30% ethyl acetate in hexane, Rf=0.8). Cold water was added and the mixture was extracted with ethyl acetate (2×50 mL) and washed with water (2×50 mL) and brine (50 mL). The organic phase was thereafter dried and concentrated to get a crude product. The crude product was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to get (1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetonitrile (399) (861 mg, 58%) as a light yellow thick oil.
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