[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[CH:5]=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].I[CH2:15][CH3:16]>O1CCCC1>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH2:15][CH3:16])[C:6]=2[CH:5]=[C:4]([Cl:11])[N:3]=1A solution of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (250 mg, 1.34 mmol) in tetrahydrofuran (4 mL) at 0° C. was treated with a 60% dispersion of sodium hydride in mineral oil (64.2 mg, 2.67 mmol) followed by iodoethane (229 mg, 1.47 mmol). After stirring at 0° C. for 0.5 h, the reaction mixture was allowed to warm to room temperature and was stirred at room temperature overnight. At this time, the resulting mixture was quenched with a saturated aqueous sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate. The combined organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (30% ethyl acetate/hexane) afforded 4,6-dichloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine (200 mg, 69.6%). LC-MS calcd. for C9H8Cl2N2 [(M)+] 214, obsd. 214.9.
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