Br[C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)=[N:6][CH:7]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=3)=[N:6][CH:7]=2)=[CH:22][CH:21]=1A mixture of PdCl2dppf (300 mg, 0.4 mmol), N-(5-bromo-3-nitro-pyridin-2-yl)-benzene-1,3-diamine (Preparation P1, 2.5 g, 8.2 mmol) and 4-fluorophenylboronic acid (1.4 g, 10 mmol) in DME (16 ml) and 2N Na2CO3 (16 ml) was deoxygenated by evacuate/fill N2 (×3), then stirred and heated at 80° C. under N2 for 4 hours. After cooling to RT the mixture was partitioned between EtOAc/H2O and then filtered through Celite. The organic layer was washed with brine (×1) then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica (10→50% EtOAc/petrol) to give the title compound (1.66 g) as a dark red/brown solid. 1H NMR (400 MHz, DMSO-d6): 9.85 (1H, s), 8.87 (1H, d), 8.70 (1H, d), 7.82 (2H, dd), 7.33 (2H, t), 7.02 (1H, t), 6.92-6.81 (2H, m), 6.40 (1H, d), 5.15 (2H, s).
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