HCID 178418361, compound → HCID 178500115, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[5-(2,4-difluorophenyl)-4-(6-hydroxy-5-nitro-2-pyridyl)-1H-imidazol-2-yl]-2-methyl-propanoate (90.0 g, 0.22 mol), wet 10% Pd/C (4.5 g), and methanol (1.77 L) are combined at 15-25° C. The reaction is stirred under 20-25 psig hydrogen atmosphere for 3-6 h. The reaction mixture is filtered over diatomaceous earth, and the filter aid is washed with methanol (227 mL). The filtrate is concentrated under reduced pressure below 40° C., and methyl tert-butyl ether (729.3 mL) is added. The MTBE is removed under reduced pressure below 40° C., and more methyl tert-butyl ether (729.3 mL) is added. The MTBE is removed under reduced pressure below 40° C. Methyl tert-butyl ether (182 mL) and methanol (46 mL) are added and the mixture heated to 50-60° C. for 1-2 h. The mixture is cooled to 10-15° C., and stirred for 2-4 h. The solids are collected by filtration and the filtercake washed with methyl tert-butyl ether (61 mL). The solids are dried under vacuum below 50° C. to furnish the title compound as a yellow solid (75.0 g, 88%).

Provenance & Evidence