Yield:-

Reaction Conditions:

with iodine;sodium hydroxide in 1,4-dioxane for 1 h;

Steps:

16.A INTERMEDIATE 16 (5-CHLOROPYRIDIN-2-YL)(4-IODO-5-METHYL-1-((2- (TRIMETHYLSILYL)ETHOXY)METHYL)-1H-IMIDAZOL-2-YL)METHANONE Step A: 4-Iodo-5-methyl-1H-imidazole:
A solution of 4-methyl-1H-imidazole (5.4 g, 65.8 mmol) and iodine (16.69 g, 65.8 mmol) in dioxane (51 ml) was treated with NaOH (132 ml, 132 mmol) for 1 h. Most organic solvent was removed under reduced pressure. It was neutralized by saturated ammonium chloride and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was triturated in 50 mL of diethyl ether and aged for 10 min. The white solids were collected by filtration and dried under vacuum to give the title compound.

References:

MERCK SHARP & DOHME CORP.;XU, Jiayi;ALI, Amjad;ZHOU, Wei;GAO, Ying-Duo;EDMONDSON, Scott, D.;MERTZ, Eric;NEELAMKAVIL, Santhosh, F.;LIU, Weiguo;SUN, Wanying;SHEN, Dong-Ming;HARPER, Bart;ZHU, Cheng;BARA, Thomas;LIM, Yeon-Hee;YANG, Meng WO2017/74832, 2017, A1 Location in patent:Page/Page column 42