Trifluoroacetic acid → [3-(4-Benzenesulfonylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

HRID 1944482노트

반응식

HRID 1944482 반응식
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].[C:17]1([S:23]([C:26]2[N:27]=[CH:28][S:29][C:30]=2[CH:31]=O)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(=O)([O-])O.[Na+].ClCCCl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:31][C:30]2[S:29][CH:28]=[N:27][C:26]=2[S:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:24])=[O:25])=[C:6]1[CH3:15]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 866522084-Benzenesulfonylthiazole-5-carbaldehyde

생성물 1

HCID 67044096[3-(4-Benzenesulfonylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester수율 48.2%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

A mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.2 g), 4-benzenesulfonylthiazole-5-carbaldehyde (0.23 g) and 1,2-dichloroethane (7.0 mL) at 0° C. was treated dropwise with a mixture of triethylsilane (2.2 mL), trifluoroacetic acid (0.6 mL) and 1,2-dichloroethane (2.0 mL), and the resulting mixture was stirred at room temperature overnight. The mixture was cooled to 0° C. and diluted with saturated aqueous sodium hydrogen carbonate solution. The phases were separated and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 1:4 by volume) to afford the title compound as a white foam (0.20 g).

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate and dichloromethane (0:1 to 1:4 by volume)

출처 및 근거

ORD 기록
ord-8c97b2c6e28c4cf296e6d38813abe197
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394836B2

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