Methyl triflate → HCID 58368388, compound

HRID 1851078Notes

Reaction equation

HRID 1851078 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:10]([CH3:24])[NH:9]2)=[CH:4][CH:3]=1.F[C:26](F)(F)S(OC)(=O)=O>ClCCl>[CH2:17]([O:16][C:14]([C:11]1[C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]([CH3:26])[C:10]=1[CH3:24])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 67229850HCID 67229850, compound

Product 1

HCID 58368388HCID 58368388, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-(4-fluorophenyl)-5-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (8.0 g, 0.024 mol) in dichloromethane (80 mL), methyl trifluoromethanesulfonate (4.8 g, 0.029 mol) was added and stirred at room temperature for 24 hours. The resulting mixture was extracted with dichloromethane and saturated baryta water. After phase separation, the aqueous layer was extracted again with dichloromethane. All the organic layers were collected, dried with Na2SO4 and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=4:1) to give the target compound (2.69 g, 32% yield).

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane and saturated baryta water
  2. customAfter phase separation
  3. extractionthe aqueous layer was extracted again with dichloromethane
  4. customAll the organic layers were collected
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=4:1)

Sources & evidence

ORD record
ord-40ed7f2fbfda467d975486d50efb7482
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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