[C:1]([C:5]1[CH:6]=[C:7]([C:10]([OH:13])=[CH:11][N:12]=1)[C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2].[CH3:14]CN(C(C)C)C(C)C.C[Si](C=[N+]=[N-])(C)C>CC#N.CO>[C:1]([C:5]1[CH:6]=[C:7]([C:10]([O:13][CH3:14])=[CH:11][N:12]=1)[C:8]#[N:9])([CH3:4])([CH3:2])[CH3:3]To a solution of 10.0 g (73.5 mmol) of 2-tert-Butyl-5-hydroxy-isonicotinonitrile ((a) J. Med. Chem. 1981, 24, 115 (b) U.S. Pat. No. 4,123,537) in MeCN/MeOH (9:1, 20 mL) was added iPr2NEt (1.48 mL, 8.52 mmol) followed by (trimethylsilyl)diazomethane (2.0 M in hexane, 4.30 mL, 8.52 mmol). The red solution was stirred 18 h at rt then concentrated. The residue was dissolved in CH2Cl2, washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated to provide 2-tert-Butyl-5-methoxy-isonicotinonitrile (1.10 g, 99%) as a pale yellow oil which was utilized without further purification.
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