Sodium hydride → 1-(4-Bromo-1-methyl-1h-pyrazol-3-yl)-2-pyrrolidinone

HRID 632766Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12]Cl)=[N:4][N:5]([CH3:7])[CH:6]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-chlorobutanamide (456 mg) in DMF (8.1 mL) was added a sodium hydride 60% dispersion in mineral oil (72 mg) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (114 mg).

Workup

temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed successively with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a3e05a929aa440fe8aa2c29b4519a5b0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321757B2

Reaction notes

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