Methyl iodide → ethyl 7-(methyl{[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

HRID 1994790

반응식

HRID 1994790 반응식
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18]2)(=[O:11])=[O:10].[C:29](=O)([O-])[O-].[K+].[K+].CI.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[CH3:29][N:12]([S:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:27])([F:1])[F:28])(=[O:11])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18]2

참가 물질

7

반응물 4

HCID 6328Methyl iodide2회HCID 8058HexaneHCID 11430Potassium CarbonateHCID 57476178ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

생성물 1

HCID 59135580ethyl 7-(methyl{[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate수율 72%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate (5.0 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (50 mL) was added methyl iodide (0.75 mL) under ice-cooling, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction solution was ice-cooled, methyl iodide (0.75 mL) was added again, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=20:80-35:65), and the obtained crude product was subjected three times to silica gel column chromatography (ethyl acetate:hexane=5:95-10:90) to give the title compound (3.7 g, yield: 72%) as a pale-yellow oil. MS: 427 (MH+).

후처리

  1. temperaturecooling
  2. temperaturecooled
  3. stirringthe mixture was stirred from under ice-
  4. temperaturecooling to room temperature for 18 hr
  5. washwashed with water, aqueous citric acid solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained crude product

출처 및 근거

ORD 기록
ord-08f687149d484c998603081a5369acca
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652133B2

연결된 노트

불러오는 중…