Trifluoroacetic anhydride → HCID 117843796, compound

HRID 2209269Notes

Reaction equation

HRID 2209269 reaction equation
[I:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]([CH3:12])([CH3:11])[C:8]([NH2:10])=O)[N:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.O>[I:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]([CH3:12])([CH3:11])[C:8]#[N:10])[N:3]=1

Participants

7

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 117843540HCID 117843540, compound

Product 1

HCID 117843796HCID 117843796, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-iodo-1H-pyrazol-1-yl)-2-methylpropanamide 7.05 (100 mg, 0.36 mmol) was dissolved in DCM (3 mL) and pyridine (1 mL). Trifluoroacetic anhydride (70 μL, 0.50 mmol) was added and the resulting mixture was stirred at r.t. for 24 h. The reaction mixture was diluted with EtOAc and water, and the phases were separated. The organic phase was washed twice with aqueous HCl (second wash remained acidic) followed by water and was dried over Na2SO4, filtered and concentrated to afford 2-(3-iodo-1H-pyrazol-1-yl)-2-methylpropanenitrile 7.07 that was used without further purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C7H9IN3: 262.0; found: 261.9.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed twice with aqueous HCl (second wash remained acidic)
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20f2a1c6680740e0bc93a616ecc2bdd9
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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