Trifluoromethanesulfonic anhydride → HCID 89350907, compound

HRID 1470513Notes

Reaction equation

HRID 1470513 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](O)=[O:13])=[CH:9][CH:8]=[C:7]2[O:15]C.C[CH2:18][N:19]([CH:23](C)C)C(C)C.[O:26](S(C(F)(F)F)(=O)=O)[S:27]([C:30]([F:33])([F:32])[F:31])(=O)=[O:28]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[S:27]([O:15][C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[C:10]([C:12](=[O:13])[N:19]([CH3:23])[CH3:18])=[CH:9][CH:8]=1)(=[O:28])=[O:26]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 71185803HCID 71185803, compound

Product 1

HCID 89350907HCID 89350907, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-chloro-4-methoxy-1-naphthoic acid (step-6 intermediate) (0.14 g, 0.561 mmol) in DCM (5 mL) was added, DIPEA (0.20 mL, 1.12 mmol) at 0° C. After 5 min stirring, Tf2O (0.11 mL, 0.67 mmol) was added to it. The resulting mixture was stirred for 2 h before quenching with ice water. The aqueous layer was extracted with DCM, and the combined organic layer was washed with, water, brine, dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography to furnish the desired trifliate intermediate as a pale yellow oil (100 mg, 47%).

Workup

  1. additionwas added
  2. customat 0° C
  3. stirringThe resulting mixture was stirred for 2 h
  4. custombefore quenching with ice water
  5. extractionThe aqueous layer was extracted with DCM
  6. washthe combined organic layer was washed with, water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c1cf468b6ce447bebd7c23c3d985c27e
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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