Bromocyclopentane → HCID 178488974, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-hydroxy-4-methoxyphenyl)-imidazole-4-formamide (110 mg, 0.47 mmol), cyclopentyl bromide (60 μl, 0.56 mmol) and K2CO3 (162 mg, 1.2 mmol) in DMF (10 ml) were heated at 70° C. overnight. A further quantity of cyclopentyl bromide (60 μl, 0.56 mmol) and K2CO3 (162 mg, 1.2 mmol) were added and the reaction mixture was cooled to room temperature, diluted with water (50 ml), extracted with ethyl acetate (2×100 ml). The combined organics were washed with brine (30 ml) dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2; CH2Cl2:EtOH (9:1) (1% NH3)) afforded 2-(3-cyclopentyloxy-4-methoxyphenyl)-imidazole-4-formamide (43 mg,) as a white solid, mp d.>195° C.

Provenance & Evidence