[CH2:1]([O:3][C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2].[N:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CC(O)=O>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:17]2[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2]A solution of 5-bromo-2-nitrophenyl ethyl ether (4.64 g, 18.86 mmol), PdCl2(dppf)*DCM (0.69 g, 0.94 mmol) and 4-pyridylboronic acid (4.03 g, 32.8 mmol) in N,N-dimethylacetamide (113 mL) was deoxygenated by bubbling with N2 (g) for ca 15 min. To this solution was added degassed 1.6 N K2CO3 (aq) (56.6 mL, 6.0 equiv.) and the resulting slurry was warmed to 80° C. for 24 h. The mixture was poured into 300 mL of H2O and neutralized with HOAc. The product was extracted with DCM, and dried (MgSO4). The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step B (3.57 g, 14.62 mmol, 77.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.66-8.70 (m, 2H), 7.97 (d, J=8.42 Hz, 1H), 7.77-7.81 (m, 2H), 7.64 (d, J=1.65 Hz, 1H), 7.47 (dd, J=8.42, 1.65 Hz, 1H), 4.33 (q, J=6.96 Hz, 2H), 1.34 (t, J=6.96 Hz, 3H).
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