Ethyl Acetate → HCID 117769926, compound

HRID 1526303Notes

Reaction equation

HRID 1526303 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.O1CCCC1.CC(C)([O-])C.[K+].Cl[CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 3035331-Chloro-2-methanesulfonylethaneHCID 66863523KOtBu THFHCID 178419412HCID 178419412, compound

Product 1

HCID 117769926HCID 117769926, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-1H-pyrazole obtained in Step C of Example 6 (600 mg) in N,N-dimethylformamide (40 mL) was added potassium tert-butoxide tetrahydrofuran solution (1 M, 6.12 mL) at room temperature, and the mixture was stirred for 10 min. To the reaction mixture was added 1-chloro-2-(methylsulfonyl)ethane obtained in Step A (873 mg) at room temperature, and the mixture was stirred for 2 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed 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 (730 mg).

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. washthe mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c605414b66564c8b8231d643ddccd33f
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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