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

HRID 1666733

Reaction equation

HRID 1666733 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-2b376ab1fdac4251a1061d6b942182c5
Source dataset
uspto-grants-2011_10
Patent number
US08044089B2

Linked notes

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