Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:21])=[N:3][CH:4]=12,5 dibromopyridine (15.0 g, 63.3 mmol) was added to toluene (450 ml) and it was cooled at −70° C. BuLi (1.6 M in hexanes)(41 ml, 66.5 mmol, 1.05 eg) was added dropwise over 1 hour, then reaction mixture was stirred at −70° C. for another hour. Benzaldehyde (7.4 g, 69.6 mmol, 1.1 eg) dissolved in toluene (5 mL) was added slowly. The mixture was stirred at −70° C. for 30 min., then warmed to 0° C. Quenched with Sat NH4Cl (200 mL) and phases partitioned. Aqueous phase was extracted with EtOAc (100 mL) and combined organic washed with brine, dried, evaporated. Residue was chromatographed with 15% EtOAc/hexane to yield the title compound.
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