Trimethylsilyl iodide → 3-(Difluoromethyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrazole-4-carboxylic acid

HRID 2279613Notes

Reaction equation

HRID 2279613 reaction equation
[F:1][CH:2]([F:20])[C:3]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]([C:13]2[N:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=2)[N:4]=1.I[Si](C)(C)C>>[F:20][CH:2]([F:1])[C:3]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]([C:13]2[N:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=2)[N:4]=1

Participants

3

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 59579960Ethyl 3-(difluoromethyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrazole-4-carboxylate

Product 1

HCID 595798213-(Difluoromethyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrazole-4-carboxylic acid

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 3-(difluoromethyl)-1-(5-fluoropyrimidin-2-yl)-1H-pyrazole-4-carboxylate (50 mg) and iodotrimethylsilane (1.0 mL) is heated at 90° C. for 4 h. The mixture is concentrated under vacuum, quenched with ice, and sodium metabisulfite is added until the aqueous solution becomes colorless. The mixture is then extracted with EtOAc (3×10 mL) and dried over anhydrous MgSO4. The dried extract is filtered and concentrated under vacuum to afford the title compound as white solid.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customquenched with ice, and sodium metabisulfite
  3. additionis added until the aqueous solution
  4. extractionThe mixture is then extracted with EtOAc (3×10 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. extractionThe dried extract
  7. filtrationis filtered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-da5d7568124242c7b478ac0bf384417a
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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