[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].I[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[Li]CCCC.CCCCCC>C1COCC1>[Br:10][C:7]1[N:8]=[CH:9][C:4]([C:1]([C:17]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)([OH:3])[CH3:2])=[CH:5][CH:6]=1A solution of 5-acetyl-2-bromopyridine (Aldrich) (1.2 g, 5.82 mmol) and 3-iodopyridine (EGA-Chemie) (1.193 g, 5.82 mmol) in THF (10 ml) was immersed in a dry ice-acetone bath. n-BuLi (1.6M) in hexane (4.00 ml, 6.40 mmol) was added slowly by a syringe at −70° C. (exothermic reaction!). The reaction was allowed to warm up slowly to room temperature and was stirred over night. The reaction mixture was cooled to −20° C. and quenched with H2O before dilution with ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo and dried to obtain title compound as off-white solid.
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