[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].[N+](C)([O-])=O.[F:19][C:20]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([F:32])[C:21]=1[C:22](Cl)=[O:23]>C(OCC)(=O)C.O.Cl.CO>[F:19][C:20]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([F:32])[C:21]=1[C:22]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[NH:8][CH:9]=1)=[O:23]
To 5-methyl-1H-pyrrolo[2,3-b]pyridine (15, 2.00 g, 15.1 mmol) and aluminum trichloride (11.6 g, 87.2 mmol), nitromethane (63.1 mL, 1.16 mol) was added, followed by the addition of 2,6-difluoro-3-nitro-benzoyl chloride (14, 3.22 g, 14.5 mmol). The reaction was placed in an oil bath at 45° C. and stirred for 3 days, then cooled to room temperature and 30 mL of methanol was added. The reaction was then diluted with 200 mL of ethyl acetate and 100 mL each of water and 1N hydrochloric acid, resulting in a precipitate that was collected to provide the desired compound (16, 2.761 g). Additional compound was recovered from the organic layer, removing the solvent and purifying by silica gel column chromatography eluting with a gradient of 5 to 70% ethyl acetate in hexanes to provide another 126 mg of compound. MS (ESI) [M+H+]+=317.9.
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