[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+]>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]>[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 (Example 146, step A) (4.5 g, 18.3 mmol), PdCl2(dppf)*DCM (1.34 g, 1.82 mmol) and 4-pyridylboronic acid (4.5 g, 36.6 mmol) in N,N-dimethylacetamide (110 mL) was deoxygenated by bubbling with N2 (g) for ca 15 min. To this solution was added degassed 1.6 N K2CO3 (aq) (55 mL, 6.0 equiv.) and the resulting slurry was warmed to 80° C. for 24 h. The N,N-dimethylacetamide was removed under reduced pressure and the solids were taken up in EtOAc, filtered to remove insoluble solids, washed with H2O, and dried (Na2SO4). The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step A (2.46 g, 10.1 mmol, 55%). 1H NMR (400 MHz, CDCl3) δ ppm 8.72 (dd, J=4.67, 1.56 Hz, 2H), 7.93 (d, J=8.06 Hz, 1H), 7.45-7.51 (m, 2H), 7.21-7.26 (m, 2H), 4.26 (q, J=6.96 Hz, 2H), 1.51 (t, J=6.96 Hz, 3H).
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