Trifluoromethanesulfonic anhydride → HCID 22646585, compound

HRID 393674Notes

Reaction equation

HRID 393674 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[Cl:16][C:17]1[CH:36]=[CH:35][C:20]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:33][CH3:34])=[C:29](O)[CH:30]=3)[N:25]=[CH:24][CH:23]=2)=[C:19]([F:37])[CH:18]=1>N1C=CC=CC=1>[Cl:16][C:17]1[CH:36]=[CH:35][C:20]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:33][CH3:34])=[C:29]([O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[CH:30]=3)[N:25]=[CH:24][CH:23]=2)=[C:19]([F:37])[CH:18]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 22646588HCID 22646588, compound

Product 1

HCID 22646585HCID 22646585, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triflic anhydride (620 mg, 2.2 mmol) was added to 4-(4-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinoline (637 mg, 2 mmol) in pyridine (6 ml) at 0° C. over 5 minutes. The mixture was stirred 1 hour and left to warm up to ambient temperature. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water containing 1M hydrochloric acid. The organic layer was dried (MgSO4), insoluble materials were removed by filtration and the volatiles were removed by evaporation. The resulting crude oil was purified by flash chromatography eluting with ethyl acetate/isohexanes (1/9 increasing to 9/1). The volatiles were removed by evaporation and the residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-trifluoromethylsulphonyloxyquinoline (560 mg, 62%).

Workup

  1. waitleft
  2. customThe volatiles were removed by evaporation
  3. customthe residue was partitioned between ethyl acetate and water containing 1M hydrochloric acid
  4. dry with materialThe organic layer was dried (MgSO4), insoluble materials
  5. customwere removed by filtration
  6. customthe volatiles were removed by evaporation
  7. customThe resulting crude oil was purified by flash chromatography
  8. washeluting with ethyl acetate/isohexanes (1/9 increasing to 9/1)
  9. customThe volatiles were removed by evaporation
  10. customthe residue was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum

Sources & evidence

ORD record
ord-19ab8d9fc92140ed83b2a22ff23eaf61
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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