C1CCC=CCCC=1.O=O.[C-:11]#[N:12].[Na+].[NH2:14][C:15]1[C:24]([CH3:25])=[CH:23][C:22](Br)=[CH:21][C:16]=1[C:17]([NH:19][CH3:20])=[O:18]>Cl[Ni]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn]>[NH2:14][C:15]1[C:24]([CH3:25])=[CH:23][C:22]([C:11]#[N:12])=[CH:21][C:16]=1[C:17]([NH:19][CH3:20])=[O:18]A reaction flask was charged with of [1,1′-bis(diphenylphosphino)ferrocene]-dichloronickel (68 mg, 0.099 mmol), zinc (130 mg, 1.99 mmol), 1,5-cyclooctadiene (28.3 mg, 0.262 mmol) and oxygen-free acetonitrile (4 mL) under a nitrogen atmosphere in a glovebox. After stirring for 2 h at room temperature, sodium cyanide (0.55 g, 11.22 mmol, ground prior to use), 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (2.43 g, 9.99 mmol) and more oxygen-free acetonitrile (8 mL) were added to the reaction mixture. The flask was removed from the glovebox while maintaining a nitrogen atmosphere, and the reaction mixture was then heated at reflux (about 82° C.) while being vigorously stirred. After about 2 h and 25 minutes, HPLC analysis of the reaction mixture indicated about 96% conversion of the 2-amino-5-bromo-N,3-dimethylbenzamide with 2-amino-5-cyano-N,3-dimethylbenzamide being the major product. A portion of the reaction mixture (0.05 mL) was withdrawn and evaporated to dryness to give an analytical sample for 1H NMR analysis.
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