Pyrazole → HCID 61631227, compound

HRID 2408225Notes

Reaction equation

HRID 2408225 reaction equation
[NH:1]1C=CC=N1.ClC1C(C(NC2C=CC=CC=2[C:22]2[CH:27]=[C:26]([F:28])[C:25]([N:29]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[N:30]3)=[C:24]([F:38])[CH:23]=2)=O)=CC=CN=1.O.O.[Sn](Cl)Cl>C(O)C>[F:38][C:24]1[CH:23]=[C:22]([NH2:1])[CH:27]=[C:26]([F:28])[C:25]=1[N:29]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[N:30]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 61436Stannous chloride dihydrateHCID 86707214HCID 86707214, compound

Product 1

HCID 61631227HCID 61631227, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(2,6-difluoro-4-nitrophenyl)-3-trifluoromethyl)-1H-pyrazole (i.e. the product of Step A; 2.39 g, 8.15 mmol) and tin(II) chloride dihydrate (9.33 g, 41.3 mmol) in ethanol (173 mL) was refluxed for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate and washed successively with 1 N aqueous sodium hydroxide, and then water. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by medium pressure liquid chromatography on silica gel eluted with 0 to 100% ethyl acetate in hexanes to provide the title compound (2.00 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed successively with 1 N aqueous sodium hydroxide
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by medium pressure liquid chromatography on silica gel
  8. washeluted with 0 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9501c6737c3041f5864d7c133f8f5aa0
Source dataset
uspto-grants-2014_08
Patent number
US08815772B2

Reaction notes

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