Trifluoroacetic acid → HCID 178516233, compound

HRID 1798818Notes

Reaction equation

HRID 1798818 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:12]CC3C=CC(OC)=CC=3)=[N:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.FC(F)(F)C(O)=O>ClCCl.CC(C)=O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([OH:12])=[N:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58128508HCID 58128508, compound

Product 1

HCID 178516233HCID 178516233, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

5-(1H-1,2,3-triazol-1-yl)-2-(4′-methoxybenzyloxy)pyridine from step 3 of this example (890 mg, 3.15 mmol) was dissolved in dichloromethane (11 ml). Trifluoroacetic acid (3.64 ml, 47.3 mmol) was added and the mixture stirred at RT. Within 10 minutes the reaction had turned light purple. The reaction mixture was evaporated 40 minutes after TFA addition, then reconstituted in CH2Cl2/heptane and evaporated again. The residue was purified by column chromatography on a Biotage 40 g SiO2 column, eluting with 0-15% methanol in CH2Cl2 to give a white solid. The white solid was suspended in acetone and filtered over celite to remove silica from the crude. The filtrate was then evaporated and pumped on high vacuum overnight to give the title compound as a complex with acetone.

Workup

  1. customThe reaction mixture was evaporated 40 minutes
  2. additionafter TFA addition
  3. customevaporated again
  4. customThe residue was purified by column chromatography on a Biotage 40 g SiO2 column
  5. washeluting with 0-15% methanol in CH2Cl2
  6. customto give a white solid
  7. filtrationfiltered over celite
  8. customto remove silica from the crude
  9. customThe filtrate was then evaporated
  10. custompumped on high vacuum overnight

Sources & evidence

ORD record
ord-e5babb303a554b91833cf5b0b3149afe
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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