[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:11]([C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17](B(O)O)[CH:18]=1)#[N:12].C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH3:10])[NH:9][C:15]1[CH:14]=[C:13]([C:11]#[N:12])[CH:18]=[CH:17][C:16]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.00 g, 6.1 mmol), 5-cyano-2-fluorophenylboronic acid (CombiBlocks; 1.00 g, 6.84 mmol), copper(II) acetate (1.1 g, 6.1 mmol) and triethylamine (2.1 mL, 15.1 mmol) in 1,2-dichloroethane (30 mL) was heated in an oil bath at 60° C. for 3 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 120 g column, eluting with 10-50% ethyl acetate/hexanes, to give N′-(5-cyano-2-fluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (700 mg, 44%) as a colorless oil.
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