Iodine → HCID 44553562, compound

Participants

Reaction Conditions

Reaction Steps

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-1H-imidazol-4-yl}benzonitrile (Example 31, 50 mg, 0.153 mmol) in THF (0.75 mL) was added freshly made LDA (0.2 mL, 0.2 mmol) at −78° C. After stirring at −78° C. for 1 h, I2 (55 mg, 0.215 mmol) was added and the reaction was warmed up to rt and stirred overnight. The reaction was quenched with aq NH4Cl, and the product was 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 column chromatography (5-20% EtOAc in hexanes) to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.20 (d, 2H), 7.65 (d, 2H), 7.28 (d, 2H), 6.99 (d, 2H), 3.62 (s, 3H). LCMS: [M+1]=451.9.

Provenance & Evidence