Trifluoromethanesulfonic anhydride → 5-Bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate

HRID 2207029Notes

Reaction equation

HRID 2207029 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.[O:15](S(C(F)(F)F)(=O)=O)[S:16]([C:19]([F:22])([F:21])[F:20])(=O)=[O:17]>ClCCl.N1C=CC=CC=1>[F:20][C:19]([F:22])([F:21])[S:16]([O:12][C:11]1[C:2]([Br:1])=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:13])[N:7]=[C:6]([CH3:14])[CH:5]=[CH:4]2)(=[O:17])=[O:15]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 666314165-Bromo-2,7-dimethylquinolin-6-ol

Product 1

HCID 866919775-Bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-bromo-2,7-dimethylquinolin-6-ol (1.04 g, 3.1 mmol) in dichloromethane (50 mL) and pyridine (10 mL) was added Tf2O (1.1 mL, 6.2 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours, quenched with slowly addition of NaHCO3 solution at 0° C. The mixture was extracted with dichloromethane. The organic layer was washed with brine, dried and concentrated to give the desired product. Column purification gave pure product. LCMS-ESI+: calc'd for C12H9BrF3NO3S: 383.9 (M+H+); Found: 383.9 (M+H+).

Workup

  1. customquenched with slowly addition of NaHCO3 solution at 0° C
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1eac5817ff6a4a2ebb63f3d760441755
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

Loading…