Toluene → HCID 44554257, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-{4-(4-bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 2 g, 4.38 mmol), (1-ethoxyvinyul)tributyltin (1.7 g, 4.82 mmol), PdCl2(PPh3)2 (67 mg, 0.2 mmol), and 15 mL of toluene under nitrogen was heated at 100° C. overnight. The reaction mixture was diluted with EtOAc, washed with H2O, brine, dried over MgSO4, filtered. To the filtrate was added KF/Celite (50% wt from Aldrich) which was stirred for 1.5 h. Upon filtration and concentration, the residue was taken up in 20 mL of EtOH and 10 mL of 2 N HCl, stirred at rt for 1 h. The precipitate was collected by filtration, washed with water and a small amount of EtOAc. The solid was further purified by silica gel column chromatography (10-50% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.62 (d, 1H), 8.38 (d, 1H), 8.26 (d, 2H), 8.19 (d, 2H), 7.83 (t, 1H), 7.31 (t, 1H), 7.23 (d, 2H), 7.04 (d, 2H), 4.13 (s, 3H), 2.61 (s, 3H). LCMS: m/z 420 (M+H)+.

Provenance & Evidence