[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[C:8]([C:11]#[N:12])[C:5]2=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:9]=[C:8]([C:11]#[N:12])[C:5]2=[N:6][CH:7]=1To mixture of 6-bromo-1H-pyrrolo[3,2-b]pyridine-3-carbonitrile (500 mg, 2.252 mmol) in N,N-dimethylformamide (4.5 mL) was added sodium hydride (60% dispersion in mineral oil) (59.4 mg, 2.477 mmol) followed by 4-(bromomethyl)tetrahydro-2H-pyran (444 mg, 2.477 mmol). The mixture was heated at 100° C. for 2 hours. The reaction was diluted with 50 mL of ethyl acetate and the organic mixture was washed with a solution of aqueous sodium bicarbonate (1×50 mL), water (1×50 mL), and brine (1×30 mL), dried over magnesium sulfate, filtered, concentrated, and purified by silica gel flash chromatography (Isco®, Redi-Sep® column) eluting with a gradient of 30-100% ethyl acetate/hexane to afford the title compound.
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