Pyridine → Methyl 3-(azepan-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403406노트

반응식

HRID 1403406 반응식
[N:1]1([C:8]2[C:9](=[O:22])[NH:10][CH:11]3[CH:16]([N:17]=2)[CH:15]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:12]3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>ClCCl>[N:1]1([C:8]2[C:9]([O:22][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:31])=[O:29])=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70665322Methyl 3-(azepan-1-yl)-2-oxo-1,2,4a,8a-tetrahydroquinoxaline-6-carboxylate

생성물 1

HCID 86670563Methyl 3-(azepan-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 3-(azepan-1-yl)-2-oxo-1,2,4a,8a-tetrahydroquinoxaline-6-carboxylate (150.0 mg, 0.50 mmol) in dichloromethane (50 mL) was added pyridine (210 mg, 2.64 mmol) and Tf2O (375 mg, 1.32 mmol) with stirring overnight under atmosphere of nitrogen at room temperature. The reaction mixture was then quenched with water (50 mL), extracted with dichloromethane (3×15 mL), the organic layers combined and dried over anhydrous magnesium sulfate, concentrated in vacuo to afford methyl 3-(azepan-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (250 mg, crude), which was used directly in the next step.

후처리

  1. customThe reaction mixture was then quenched with water (50 mL)
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-204ad910275b426db9a56afbecd5d14c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912188B2

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