1-(Bromomethyl)-2-(trifluoromethyl)benzene → HCID 59547893, compound

HRID 1946366Notes

Reaction equation

HRID 1946366 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:5].CC(C)([O-])C.[K+].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>CN(C)C=O.C(#N)C>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[C:24]([F:23])([F:33])[F:34])[N:8]=1)=[O:5]

Participants

6

Reactant 3

HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 23665647Potassium tert-butoxideHCID 178522346HCID 178522346, compound2×

Product 1

HCID 59547893HCID 59547893, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide ((for a preparation see Intermediate 9)(31.9 mg, 0.1 mmol) in dimethylformamide (0.4 ml) was treated with potassium t-butoxide (11.3 mg, 0.1 mmol) and allowed to stand at room temperature for 10 min. A solution of 2-(trifluoromethyl)benzyl bromide (22.3 mg, 0.1 mmol, Aldrich) in acetonitrile (0.2 ml) was finally added and the solution left to stand for 16 h at room temperature. The solvent was removed using a Genevac and the crude mixture dissolved in a 1:1 mixture of dimethylsulphoxide:methanol (0.6 ml) and the solution purified by MDAP on SUNFIRE C18 (Method D). The appropriate fraction was concentrated in vacuo using a Genevac to give the title compound (2.3 mg);

Workup

  1. waitthe solution left
  2. waitto stand for 16 h at room temperature
  3. customThe solvent was removed
  4. dissolutionthe crude mixture dissolved in a 1:1 mixture of dimethylsulphoxide
  5. custommethanol (0.6 ml) and the solution purified by MDAP on SUNFIRE C18 (Method D)
  6. concentrationThe appropriate fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-01955f0dde53486bb6920b81b324679d
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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