Sodium hydride → HCID 86592858, compound

Participants

Reaction Steps

To a solution of 4-[3-ethoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenol (515.5 mg) in DMF (5 ml) was added sodium hydride 60% dispersion in mineral oil (79.7 mg) at 3° C. The mixture was stirred at ambient temperature for 40 minutes. To the reaction mixture was added a solution of tert-butyl (2-bromoethyl)carbamate (558 mg) in DMF (2 ml). The mixture was stirred at 60° C. for 24 hours. The reaction mixture was poured into ice water and was extracted with AcOEt. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was crystallized from AcOEt, collected and washed with IPE to give 1st crop of tert-butyl (2-{4-[3-ethoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)carbamate (344 mg) as a white powder. The mother liqour was concentrated in vacuo and purified by silica gel column chromatography eluted with AcOEt/CHCl3=10% to give 2nd crop of tert-butyl (2-{4-[3-ethoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)carbamate (218 mg ) as a powder.

Provenance & Evidence