Trifluoromethanesulfonic anhydride → Pyridin-4-yl trifluoromethanesulfonate

HRID 2209094Notes

Reaction equation

HRID 2209094 reaction equation
C[Si](C)(C)CCOCN1C=C([C:12]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][N:13]=2)C=N1.[O:21](S(C(F)(F)F)(=O)=O)[S:22]([C:25]([F:28])([F:27])[F:26])(=O)=[O:23]>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[S:22]([O:18][C:16]1[CH:15]=[CH:14][N:13]=[CH:12][CH:17]=1)(=[O:23])=[O:21]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 178504229HCID 178504229, compound

Product 1

HCID 18424478Pyridin-4-yl trifluoromethanesulfonateYield 123.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyridin-4-ol (0.67 g, 2 mmol) in DCM was added TEA (0.69 g, 7 mmol) and the mixture was stirred at OC, (Tf)2O (0.843 g, 3 mmol) was added slowly. The resulting reaction mixture was steered at r.t. for one hour. Solvent was removed under vacuo. And the residue was purified by silicone gel column to afford 2414(2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyridin-4-yl trifluoromethanesulfonate (0.56 g, 58%) LCMS-ESI+ (m/z): [M+H]+ calcd. for C26H30N5O3: 424.48; found: 424.05.

Workup

  1. additionwas added slowly
  2. customThe resulting reaction mixture
  3. customSolvent was removed under vacuo
  4. customAnd the residue was purified by silicone gel column

Sources & evidence

ORD record
ord-f56aa9bd71e64ea78772f7fc41e78be0
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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