[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1.[OH-].[NH4+]>[Pd].CO.CCOC(C)=O>[NH4+:13].[OH-:2].[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1A mixture of 3-(3-cyano-phenyl)-2-methyl-propionic acid methyl ester of Step B (62 mg, 0.30 mmol) and palladium on carbon (10%, 50 mg) in MeOH (10 mL), EtOAc (10 mL), and ammonium hydroxide (5 mL) was hydrogenated at 40 psi for 24 h. The catalyst was removed via filtration through Celite with the aid of MeOH. The solvent was removed in vacuo. Chromatography (1:1 hexanes:EtOAc to CH2Cl2:MeOH:NH4OH, 95:5:0.1) provided the title compound of Step C (45 mg). 1H NMR (400 MHz, CD3OD) δ 7.31-7.14 (m, 4H), 3.94 (s, 2H), 3.59 (s, 3H), 2.96 (m, 1H), 2.72 (m, 2H), 1.12 (d, 3H); MS 208 (M+1).
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