Iodoethane → HCID 70980817, compound

Participants

Reaction Conditions

Reaction Steps

[1-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (370 mg, 0.66 mmol) was dissolved in THF (8 mL) and cooled to −78° C. LiHMDS (1 M solution in THF, 2 mL, 1.98 mmol) was added and the mixture stirred at −78° C. for 15 minutes. Iodoethane (160 mL, 1.98 mmol) was then added to the mixture, the cooling bath removed and then stirring continued for a further 15 minutes, during which time, the mixture reached ambient temperature. Saturated aqueous ammonium chloride and EtOAc were added. The EtOAc layer was isolated and washed with dilute aqueous potassium hydrogen phosphate solution. The EtOAc layer was then washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using SiO2 chromatography (10-30% EtOAc/Petrol) to give [1-(4-chloro-phenyl)-3,3-diethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (145 mg). MS: [M+H]+ 582.

Provenance & Evidence