Sodium hydride → HCID 19955590, compound

Participants

Reaction Steps

Methyl 2-butyl-4-chloro-1H-imidazole-5-carboxylate (0.19 g) was added to a stirring suspension of sodium hydride (60% dispersion in mineral oil; 35 mg) in dry dimethylformamide (2 ml) at ambient temperature under a nitrogen atmosphere and stirring was continued for 30 minutes. A solution of 3-(4'-bromomethylbiphenyl-2-yl)-4-isopropoxycyclobut-3-ene-1,2-dione (0.64 g; preparable as in Example 1(c)) in dry dimethyl formamide (3 ml) was added and stirring was continued for 24 hours. The reaction mixture was partitioned between water (20 ml) and diethyl ether (20 ml), and the aqueous layer was separated and extracted with diethyl ether (20 ml). The combined ether solutions were dried over magnesium sulphate and the solvent was evaporated in vacuo. The residue obtained was purified by flash chromatography on silica gel (eluting with 20% ethyl acetate in petroleum ether (b.p. 40°-60° C.)) to give methyl 2-butyl-4-chloro-1-[2'-(2-isopropoxy-3,4-dioxocyclobut-1-en-1-yl)biphenyl-4-ylmethyl]-1H-imidazole-5-carboxylate, an active compound of the present invention, as a yellow oil (0.17 g).

Provenance & Evidence