[N+](C1C=C[N+]([O-])=C2NC=CC=12)([O-])=O.[N+:14]([C:17]1[C:25]2[C:20](=[N+:21]([O-])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)([O-:16])=[O:15].CS([Cl:31])(=O)=O>CN(C)C=O>[Cl:31][C:24]1[CH:23]=[CH:22][N:21]=[C:20]2[NH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[C:25]=12To a solution of a 2:1 mixture (589.8 mg) of 4-nitro-1H-pyrrolo-[2,3-b]pyridine 7-oxide and 3-nitro-1H-pyrrolo[2,3-b]pyridine-7-oxide in N,N-dimethylformamide (6 ml) was added dropwise methanesulfonyl chloride (0.68 ml) at 65° C. The reaction mixture was stirred at 65° C. for 2 hours. The reaction mixture was quenched with water (30 ml) under ice cooling, and neutralized (pH ˜6.5) with 20% NaOH solution. The resulting precipitates were collected by filtration, dried in vacuo at 40° C., and washed with EtOAc to give 4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine (172.8 mg) as a brown solid.
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