[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[C:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([CH3:23])[CH:21]=2)[NH:16][CH:15]=1)=[O:13].C(OCC)(=O)C.C(=O)(O)[O-]>O>[NH2:8][C:7]1[C:2]([F:1])=[C:3]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH3:23])[CH:21]=3)[NH:16][CH:15]=2)=[O:13])[C:4]([F:11])=[CH:5][CH:6]=1To (2,6-difluoro-3-nitro-phenyl)-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (16, 1.165 g, 3.672 mmol), 80 mL of ethyl acetate was added, followed by stannous chloride, dihydrate (2.86 g, 12.6 mmol). The suspension was stirred in an oil bath at 65° C. for 18 hours, then poured into a beaker with 200 mL each of water and saturated bicarbonate. The resulting milky suspension was treated with celite, then vacuum filtered through a thin pad of celite. The resulting clear layers of the filtrate were separated and the solvents were removed from the ethyl acetate layer. The resulting material was purified by silica gel column chromatography eluting with a gradient from 30 to 100% ethyl acetate in hexanes to give the desired compound with some impurities. This material was re-purified by silica gel column chromatography eluting with a gradient from 1 to 60% methanol in dichloromethante to give the desired compound (17, 760 mg). 1H NMR was consistent with the desired compound structure. MS (ESI) [M+H+]+=288.5.
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