[Br:1][C:2]1[C:3]([CH2:15][CH3:16])=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30]>C(#N)C>[Br:1][C:2]1[C:3]([CH2:15][CH3:16])=[C:4]([CH:8]=[C:9]2[CH2:10][CH2:11][N:12]([CH2:30][CH2:29][C:28]([O:32][CH2:33][CH3:34])=[O:31])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1To a solution of 4-[(3-bromo-2-ethylphenyl)methylidene]piperidine (D137) (1 g, 3.57 mmol) in Acetonitrile (10 mL) was added DBU (0.807 mL, 5.35 mmol) and ethyl 2-propenoate (0.429 g, 4.28 mmol). The reaction solution was heated to 60° C. for overnight. The solvent was removed in vacuo and the residue was diluted with ethyl acetate, washed with water, dried and concentrated to afford ethyl 3-{4-[(3-bromo-2-ethylphenyl)methylidene]-1-piperidinyl}propanoate (D138) (1.35 g), which was used directly without further purification. MS (ES): C19H26BrNO2 requires 379.1. found 380.1 (M+H+).
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