Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[NH:9]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1.CCCCCCC=CCCC>C1COCC1.C(OCC)(=O)C>[Br:8][C:4]1[N:3]=[C:2]([N:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[CH:7]=[CH:6][CH:5]=1A mixture of 2,6-dibromopyridine (2.37 g, 0.01 mol), pyrrolidin-3-ol (1.0 g, 0.01 mol), 1,8-diazabicclo[5.4.0)-7-undecene (1.5 mL) in 10 mL of THF was heated at 70° C. under a nitrogen atmosphere for 11 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate (30 mL). The resulting solution was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (10-30% ethyl acetate/hexane) to give the title compound.
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