Pyridine → acetic acid (5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-methyl ester

HRID 2191447노트

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HRID 2191447 반응식
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[F:12].N1C=CC=CC=1.Cl[C:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])=[O:21]>O1CCCC1>[F:12][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][C:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])=[O:21])[NH:8][C:7](=[O:11])[CH2:6]2

참가 물질

5

반응물 3

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 101035046-Amino-5-fluoroindolin-2-one

생성물 1

HCID 59250091acetic acid (5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-methyl ester수율 70.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

6-Amino-5-fluoro-1,3-dihydro-indol-2-one 3d (500 mg, 3.0 mmol) was dissolved in 10 ml of tetrahydrofuran under stirring, and added with 0.4 ml of pyridine to the solution at room temperature. After stirring to mix well, the mixture was cooled down to −40° C. in a dry ice-acetone bath. A solution of acetic acid chlorocarbonylmethyl ester (420 mg, 3.0 mmol) in 10 ml of tetrahydrofuran was added dropwise to the above reaction system. Upon completion of the addition, the dry ice-acetone bath was removed, and the reaction mixture was allowed to warm up to room temperature and stirred overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered. The resulting solid was washed with water for three times and dried to obtain the title compound acetic acid (5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-methyl ester 27a (562 mg, yield 70.4%) as a gray solid.

후처리

  1. stirringAfter stirring
  2. additionto mix well
  3. additionUpon completion of the addition
  4. customthe dry ice-acetone bath was removed
  5. temperatureto warm up to room temperature
  6. stirringstirred overnight
  7. filtrationthe reaction mixture was filtered
  8. washThe resulting solid was washed with water for three times
  9. customdried

출처 및 근거

ORD 기록
ord-a859b34d98264d77a571d29e6cc4ff77
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329682B2

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