Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:13]([CH3:12])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:3][CH:4]=1)=[O:7]According to the general procedure B, methyl 4-chlorobenzoate (172 mg, 1.00 mmol) reacted with N-methylaniline (130 mg, 1.20 mmol) using 1 mol % of Pd(OAc)2, 2 mol % of Ph5FcP(t-Bu)2, and K3PO4 (640 mg, 3.02 mmol) in DME at 100° C for 20 h to give the title compound (240 mg, 97%) as a solid: 1H-NMR (500 MHz, CDCl3): δ 7.89 (d, 2H, J=9.05 Hz), 7.41 (t, 2H, J=7.68 and 8.17 Hz), 7.24-7.21 (m, 3H), 6.79 (d, 2H, J=9.06 Hz), 3.88 (s, 3H), 3.37 (s, 3H). 13C{1H}-NMR (125 MHz, CDCl3): δ 167.09, 152.44, 147.41, 130.91, 129.70, 125.50, 125.24, 119.08, 113.70, 51.47, 40.09. GC/MS(EI): m/z 241 (M+). Anal. Calcd for C15H15NO2: C, 74.67; H, 6.27; N, 5.81. Found: C, 74.74; H, 6.34; N, 5.80.
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