Trifluoroacetic acid → 3-(1H-pyrazol-4-yl)benzonitrile trifluoroacetate

HRID 1962721Notes

Reaction equation

HRID 1962721 reaction equation
C[Si](C)(C)CCOC[N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[CH:9]=[N:8]1.[C:22]([OH:28])([C:24]([F:27])([F:26])[F:25])=[O:23]>>[F:25][C:24]([F:27])([F:26])[C:22]([OH:28])=[O:23].[NH:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[CH:9]=[N:8]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574776673-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrazol-4-yl)benzonitrile

Product 1

HCID 665974043-(1H-pyrazol-4-yl)benzonitrile trifluoroacetate

Conditions

Temperature
120 °C

Procedure

A solution of 3-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrazol-4-yl)benzonitrile (110.0 mg, 0.0003673 mol) was taken up in TFA (3.0 mL, 0.039 mol) and the mixture was heated in microwave at 120° C. for 3 min. The reaction mixture was allowed to cool to rt, and then concentrated to give a crude residue. The product was purified by HPLC on a C-18 column eluting with a water/ACN gradient containing 0.2% TFA to give 3-(1H-pyrazol-4-yl)benzonitrile trifluoroacetate as an amorphous white solid, LC/MS (M+H)+: 170.

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated
  3. customto give a crude residue
  4. customThe product was purified by HPLC on a C-18 column
  5. washeluting with a water/ACN gradient
  6. additioncontaining 0.2% TFA

Sources & evidence

ORD record
ord-c46d714b15204cfc8b396eef15a83180
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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