[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=2)=[CH:6][CH:5]=1.[H][H]>CO.[Pd]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1To a stirred solution of 4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine, HCl (3 g, 13.3 mmol) (from step B) in methanol (20 mL) was added 10% palladium on carbon (1.4 g) and the reaction mixture was stirred at 20 psi of hydrogen for 12 h. The reaction mixture was filtered through a pad of celite, which was washed with ethyl acetate, and the combined organic fractions were concentrated to obtain a white solid (2 g, 70% yield). LCMS (ES-API), m/z 192.1 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 9.13-8.36 (m, 2H), 7.14 (d, J=8.7 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 3.73 (s, 3H), 3.07-2.87 (m, 4H), 2.87-2.65 (m, 4H).
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