Trifluoromethanesulfonic anhydride → Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate

HRID 472790노트

반응식

HRID 472790 반응식
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[C:27]([O:29][CH3:30])=[O:28].C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[C:27]([O:29][CH3:30])=[O:28])(=[O:5])=[O:4]

참가 물질

6

반응물 3

HCID 67749Trifluoromethanesulfonic anhydride2회HCID 516892Sodium BicarbonateHCID 57440941Methyl 3-hydroxyquinoline-8-carboxylate

생성물 1

HCID 58056975Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate수율 91%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

Trifluoromethanesulfonic anhydride (0.55 mL, 3.4 mmol) was added to a solution of methyl 3-hydroxyquinoline-8-carboxylate (650 mg, 3.2 mmol) in pyridine (2.3 mL) and CH2Cl2 (13 mL) at 0° C. The reaction mixture was allowed to warm to room temperature. After 3 h, additional trifluoromethanesulfonic anhydride (0.55 mL, 3.4 mmol) was added and the reaction was stirred for an additional 18 h. Saturated aqueous NaHCO3 (20 mL) was added and the layers were separated. The aqueous phase was extracted with CH2Cl2 (3×). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified on silica gel eluting with CH2Cl2 to afford 971 mg (91%) of methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified on silica gel eluting with CH2Cl2

출처 및 근거

ORD 기록
ord-4a8e6bba1a38401f95540a4a7f4a9cd5
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633220B2

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