Sodium hydride → HCID 10291825, compound

HRID 558259Notes

Reaction equation

HRID 558259 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[O:13][C:14]1[C:15]([CH2:21][CH3:22])=[N:16][NH:17][C:18]=1[CH2:19][CH3:20]>CN(C=O)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:16]1[C:15]([CH2:21][CH3:22])=[C:14]([O:13][C:12]2[CH:23]=[C:24]([Cl:26])[CH:25]=[C:10]([Cl:9])[CH:11]=2)[C:18]([CH2:19][CH3:20])=[N:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 9878953HCID 9878953, compound

Product 1

HCID 10291825HCID 10291825, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl bromoacetate (984 μL, 10 mmol) and then sodium hydride (60% dispersion in oil, 801 mg, 20.1 mmol) were added to a stirred solution of the pyrazole (2.6 g, 9.12 mmol) of Example 3 in dry N,N′-dimethylformamide (25 ml) at 0° C. under nitrogen. After stirring for 1 hour at 0° C. ice-water (100 ml) was added and the mixture was extracted with ether (3×50 ml). The combined ether layers were dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (20:80, by volume) to provide the title compound (780 mg) as a yellow oil which partly crystallised on standing.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether (3×50 ml)
  3. dry with materialThe combined ether layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (20:80, by volume)

Sources & evidence

ORD record
ord-bf332bb5159245ccb745c04b004f5b43
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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