Dimethylformamide → HCID 86720827, compound

HRID 877326Notes

Reaction equation

HRID 877326 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[H-].[Na+].Br[CH2:14][CH2:15][CH:16]1[O:20][CH2:19][CH2:18][O:17]1.[CH3:21]N(C=O)C>>[O:17]1[CH2:18][CH2:19][O:20][CH:16]1[CH2:15][CH2:14][CH2:21][N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 86720827HCID 86720827, compoundYield 59%

Procedure

To an ice-cooled stirred solution of ethyl 1H-pyrazole-4-carboxylate (2.0 g, 14.3 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.68 g, 17.1 mmol). The reaction mixture was allowed to warm to RT over 20 minutes and 2-(2-bromoethyl)-1,3-dioxolane (2.84 g, 15.7 mmol) added. The reaction mixture was heated at 60° C. for 16 hours. The reaction was partitioned between ethyl acetate and brine. The organic phase was washed with further brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (2.14 g, 59%).

Workup

  1. temperatureThe reaction mixture was heated at 60° C. for 16 hours
  2. customThe reaction was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with further brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated at reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 0-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-75fc2d24fe7845d9942496cbf34db78d
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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