[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:16].CO>ClCCl>[CH3:1][C:2]1[C:10]2[C:5](=[N+:6]([O-:16])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1A little at a time, 3.00 g (22.70 mmol) of 3-methyl-1H-pyrrolo[2,3-b]pyridine (Hands, David; Bishop, Brian; Cameron, Mark; Edwards, John S.; Cottrell, Ian F.; Wright, Stanley H. B.; Synthesis 1996, 877-882.) are added to a solution of 10.45 g (45.40 mmol) of meta-chloroperoxybenzoic acid in 250 ml of dichloromethane, and the mixture is stirred at 10° C. for 2 h. Addition of methanol gives a clear solution which is subjected directly to column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:4 to 3:1). A further purification step by preparative HPLC yields the target compound.
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