C([Li])CCC.Br[C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]#N)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.[OH2:29]>C(OCC)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]([C:7]3[CH:8]=[N:9][C:10]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:29])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1A solution of n-butyl lithium (1.6 M in hexanes, 1.5 ml) was added to 3-bromoquinoline (CAS Reg. No. 5332-24-1) (500 mg) in diethyl ether (16 ml) at −78° C. The mixture was stirred at −78° C. for 1 h. A solution of 1-(4-chlorophenyl)-1-cyclopropanecarbonitrile (CAS Reg. No. 64399-27-5) (427 mg) in 3 ml diethyl ether was added at −78° C. to the red mixture and then stirred for 15 min at −78° C. The mixture was allowed to warm to room temperature, then poured into water (40 ml) and extracted with diethyl ether. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 0:100-20:80, then ethyl acetate/DCM 0:100-10:90) to give the title compound as a light yellow oil (100 mg). MS (m/e)=308.3 [M+H+].
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