Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.FC(F)(F)S(O[CH2:21][C:22]([F:25])([F:24])[F:23])(=O)=O.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:21][C:22]([F:25])([F:24])[F:23])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1To a mixture of 4-(4-bromophenyl)piperidine hydrochloride (5 g, 18.1 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (4.62 g, 19.9 mmol) in ACN (250 mL) was added N,N-diisopropylethyl amine (11 mL, 63.2 mmol). The reaction mixture was heated at 45° C. for 50 min. 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.46 g, 2.0 mmol) was added and heating continued for 1 h. Another 0.46 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.0 mmol) was added and heating continued for 1 h. The reaction mixture was concentrated, diluted with brine and extracted twice with a mixture of hexanes-EtOAc-DCM. The organic layers were combined, concentrated, diluted with toluene and concentrated again. Purification by flash chromatography on silica gel (0 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 322.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=8.4 Hz, 2 H),7.08 (d, J=8.4 Hz, 2 H),3.06 (m, 2 H),3.00 (q, J=9.7 Hz, 2 H),2.45 (m, 3 H).1.77 (m, 4H).
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