Sodium hydride → N-[3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-yl]-N-propyl-propionamide

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Reaction Steps

N-(3-(2,4-Dichlorophenyl)-2,6-dimethylpyrazolo[5,1-b]oxazol-7-yl) propionamide (634 mg, 1.800 mmol) is suspended in dry DMF (20 ml) and treated with NaH (60% in oil) (86 mg, 2.160 mmol) under N2 at RT. The mixture is stirred at RT for 10 minutes before cooling to 0° C. in an ice bath. 1-Iodopropane (0.263 ml, 2.70 mmol) is added dropwise and the reaction mixture is stirred at 0° C. for 1 hr. The solvent is removed in vacuo and the resulting residue is dissolved in EtOAc and washed with 1M NaOH, 1M HCl, H2O, brine, dried (MgSO4) and evaporated down to give a brown oil. Purification by chromatography on silica eluting with 0% to 50% EtOAc/iso-hexane affords the title compound as a clear oil; MS: m/z 394.1 [M+H]+

Provenance & Evidence