Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CCO.C1(C)C=CC=CC=1.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]>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([CH3:10])[CH:9]=2)=[CH:18][CH:17]=1
A mixture of 2-bromo-4-methyl-5-nitro-benzonitrile (522.0 mg, 2.17 mmol), 4-methoxyphenyl boronic acid (329.0 mg, 2.17 mmol) and 2N aqueous potassium carbonate (6.56 mL, 13.1 mmol) in EtOH (6 mL) and toluene (3 mL) was degassed with N2 for 5 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (180.0 mg, 0.22 mmol), and degassed with N2 for an additional 5 minutes. The reaction mixture was sealed and heated to 80° C. for 3 hours. The reaction was cooled to room temperature and the layers were separated. The organic layer was filtered and the solids were air dried to give the title compound (145 mg). The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (25-75% EtOAc/heptane) to give the title compound (337 mg). The two lots of the title compound were combined (482 mg, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.59 (s, 1H), 7.78 (s, 1H), 7.63 (d, J=8.78 Hz, 2H), 7.14 (d, J=8.59 Hz, 2H), 3.85 (s, 3H), 2.64 (s, 3H).
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