[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH3:1][C:2]1[C:7]([O:8][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1A suspension of 810 mg (3.45 mmol) of 2-methyl-3-hydroxy-6-iodopyridine (from Step A), 533 μL (4.48 mmol) of benzyl bromide, 953 mg (6.89 mmol) of potassium carbonate and catalytic amount of tetrabutylammonium iodide in 10 mL of acetone was refluxed for 3 h and cooled to rt. Solid was filtered off through a cake of Celite and washed with EtOAc, and the filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 1:19 v/v EtOAc/hexanes as the eluant afforded 1.03 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.48 (s, 3H), 5.04 (s, 2H), 6.79 (d, J=8.4, 1H), 7.32-7.42 (m, 6H).
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