CCCCC.[H-].[Na+].[Br:8][C:9]1[N:14]=[C:13]2[CH2:15][C:16](=[O:18])[NH:17][C:12]2=[CH:11][CH:10]=1.Cl[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:22][N+:21]=1[O-:33]>CN(C=O)C>[Br:8][C:9]1[N:14]=[C:13]2[C:15]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)=[CH:22][N+:21]=3[O-:33])=[C:16]([OH:18])[NH:17][C:12]2=[CH:11][CH:10]=1To a suspension of previously pentane-washed sodium hydride on mineral oil (75 mg, 1.88 mmol) in DMF (2 mL) was added slowly 5-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (300 mg, 1.41 mmol). The resulting green solution was further stirred for 10 minutes at RT. Then a solution of 215 mg (0.939 mmol) of 2-chloro-5-(morpholinomethyl)-pyridine 1-oxide prepared like in example 2.2 in DMF was added and the resulting mixture was heated to 130° C. and stirred for further 30 min. The reaction was cooled to RT and all volatiles were removed under reduced pressure. The residue was taken up in 2 M HCl (60 mL) and washed with ethyl acetate. The aqueous layer was carefully saturated with solid NaHCO3 and extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered, and evaporated yielding the titled compound as a red oil.
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