p-Toluenesulfonic acid → 4-Tert-Butyl-N-(5-Hydroxy-4-Methyl-2-(2-Oxo-3-Phenylindolin-3-Yl)Phenyl)Benzenesulfonamide

HRID 16622

반응식

HRID 16622 반응식
O[C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([OH:39])[CH:33]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC(Cl)C>[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:33]=[C:34]([OH:39])[C:35]([CH3:38])=[CH:36][C:37]=2[C:2]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]2=[O:11])(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-oneHCID 8380834-tert-butyl-N-(3-hydroxy-4-methylphenyl)benzenesulfonamide

생성물 1

HCID 104145404-Tert-Butyl-N-(5-Hydroxy-4-Methyl-2-(2-Oxo-3-Phenylindolin-3-Yl)Phenyl)Benzenesulfonamide수율 89.4%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

As another non-limiting example, 4-tert-butyl-N-[5-hydroxy-4-methyl-2-(2-oxo-3-phenyl-2,3 -dihydro-1H-indol-3-yl)-phenyl]-benzenesulfonamide (compound 1430) was synthesized by adding dropwise 4-tert-butyl-benzenesulfonyl chloride (8 g, 34 mmol) in 5 mL dichloromethane to a stirring solution of 5-Amino-2-methyl-phenol (4 g, 32 mmol) in 20 mL pyridine and letting the mixture spin overnight at room temperature. The resulting mixture was concentrated in vacuo and the product was purified by column chromatography to yield 8 g (78%) of 4-tert-butyl-N-(3-hydroxy-4-methyl-phenyl)-benzenesulfonamide. A mixture of 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one (3.9 g, 17 mmol), 4-tert-butyl-N-(3-hydroxy-4-methyl-phenyl)-benzenesulfonamide (7 g, 22 mmol) and p-toluenesulfonic acid (6.5 g, 32 mmol) in dichloroethane was refluxed for 12 hours. The resulting mixture was cooled to room temperature to yield a colorless solid. The solid was filtered and purified using column chromatography to yield 8 g (88%) of the desired product (compound 1430).

후처리

  1. temperaturewas refluxed for 12 hours
  2. customto yield a colorless solid
  3. filtrationThe solid was filtered
  4. custompurified

출처 및 근거

ORD 기록
ord-54e5185f5a094c69b8faead1cbb2d43a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737172B2

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