Iodine → HCID 44554077, compound

Participants

Reaction Conditions

Reaction Steps

To 2-{4-(4-bromophenyl)-5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-2-yl}pyridine (Example 15, 150 mg, 0.33 mmol) in THF (1 mL) was added BuLi (2.5 M in hexanes, 0.17 mL, 0.427 mmol) at −78° C. After stirring at −78° C. for 0.5 h, I2 (167 mg, 0.657 mmol) was added and the reaction was allowed to warm up to rt overnight. The reaction was quenched with aq NH4Cl, extracted with EtOAc. The combined extracts were washed with aq Na2S2O3, water, and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (1-20% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.64 (d, 1H), 8.38 (d, 1H), 7.87 (d, 2H), 7.85 (t, 1H), 7.78 (d, 2H), 7.38 (t, 1H), 7.25 (d, 2H), 7.03 (d, 2H), 4.11). LCMS: [M+1]=504.

Provenance & Evidence