[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].Cl.[CH3:14][N:15](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])#[N:15]A solution of methyl 3-hydroxy-4-iodobenzoate (2.38 g, 7.0 mmol) (as described in Step B) and Zn(CN)2 (0.575 g, 4.9 mmol) in DMF was degassed with argon for 25 minutes. Pd(Ph3P)4 (0.404 g, 0.35 mmol) was added and the mixture heated to 80° C. for 16 hr. The mixture was poured into 1N HCl and extracted with EtOAc (2×), washed with water then brine, dried (MgSO4) and the solvent removed. Chromatography of the residue (silica gel; hexane:EtOAc 9:1) afforded the title compound as a white solid.
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