C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([Zn]CC)C.CCCCCC.Br[C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][C:39]([C:45]([OH:47])=[O:46])=[CH:40]2.[CH3:48][N:49]1CCCC1=O>CC([O-])=O.CC([O-])=O.[Pd+2].[C-]#N.[C-]#N.[Zn+2]>[C:48]([C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][C:39]([C:45]([OH:47])=[O:46])=[CH:40]2)#[N:49]A solution of Pd(OAc)2 (0.012 g, 0.054 mmol) and tri-o-tolylphosphine (0.073 g, 0.240 mmol) in degassed N-methylpyrrolidone (2 mL) is heated at 60° C. for 30 minutes. A solution of 1.0 M diethylzinc in hexane (0.11 mL, 0.11 mmol) is then added and stirring is continued for additional 30 minutes. To this mixture is added a mixture of 5-bromo-naphthalene-2-carboxylic acid, 1, (0.135 g, 0.536 mmol) and Zn(CN)2 (0.063 g, 0.536 mmol) in degassed N-methylpyrrolidone (2 mL). The resulting mixture is heated at 60° C. for 18 hrs. The reaction mixture is cooled and directly loaded to a prep-HPLC column eluting with CH3CN—H2O (0.1% TFA) to afford 0.085 g (80% yield) of the desired product as a white solid. m.p. 250° C. (dec.). 1H NMR (300 MHz, CDCl3): δ 8.61 (s, 1H), 8.18 (m, 2H), 8.14 (d, J=8.7 Hz, 1H), 7.94 (d, J=7.2 Hz, 1H), 7.54 (t, J=8.4 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 168.4, 134.9, 134.8, 134.5, 132.4, 131.9, 129.9, 128.5, 125.9, 125.5, 117.5, 110.2.
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