Trifluoroacetic acid → HCID 178505559, compound

HRID 1023459Notes

Reaction equation

HRID 1023459 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9](CC3C=CC(OC)=CC=3OC)[CH:10]=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][CH:10]=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86673612HCID 86673612, compound

Product 1

HCID 178505559HCID 178505559, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-[3-(2,4-dimethoxy-benzyl)-5-(4-fluoro-phenyl)-3H-imidazol-4-yl]-pyridine (720 mg, 1.54 mmol) is dissolved in DCM (12 mL) and trifluoroacetic acid (3.0 mL) is added at room temperature. The mixture is stirred for 60 hrs before saturated NaHCO3 aqueous solution is used to adjust the pH to about 7.5. Then the mixture is extracted with EtOAc (3×30 mL). The organic layers are combined and concentrated to give the crude product. The crude is purified by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) to give 316 mg of desired product.

Workup

  1. extractionThen the mixture is extracted with EtOAc (3×30 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customThe crude is purified by silica flash column chromatography

Sources & evidence

ORD record
ord-3978d4a64a9a4f2c87e8064c6c628482
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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