[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](F)[CH:9]=1)[C:5]#[N:6].[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1.C(N(CC)CC)C.CN(C)C(=O)C>CCOC(C)=O.O>[Br:1][C:2]1[CH:9]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]2)[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1
A mixture of 3-bromo-5-fluorobenzonitrile (1.6 g, 7.8 mmol), piperidine-4-carboxylic acid (2.6 g, 12.0 mmol), triethylamine (4.0 mL, 28.5 mmol) and N,N-dimethylacetamide (1.5 mL) in a sealed tube was heated to 130° C. for 48 hr. The reaction mixture was diluted with EtOAc and water. The organic layer was separated, dried (MgSO4), and concentrated to give a crude reside which was purified by chromatography on silica gel (CH2Cl2/MeOH) to afford 1-(3-bromo-5-cyanophenyl)piperidine-4-carboxylic acid.
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