[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[Cl:13][C:14]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]SC1SCC(=O)N=1>O1CCCC1>[Cl:13][C:14]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1Under a nitrogen atmosphere, add 152 mg. 2-picoline and 1.5 ml. tetrahydrofuran (THF) and cool to -28° C. Add 104 mg. n-butyl lithium and stir about 30 minutes at -78° C. Add 20 mg. of the iodide prepared in Examples 2 and 3 in 1 ml. THF. Stir 1 hour at -78° C., let warm to room temperature and stir about 15 hours. Work up with water and methylene chloride then wash with water and brine then dry over sodium sulfate. Elute on a coarse silica column with methylene chloride then 50% ethylacetate/methylene chloride to obtain the title compound. Prepare the hydrochloride salt by reaction of the title compound with 0.1N HCl.
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