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Water → 2-[(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-oxo-1,6-dihydropyridin-2-yl)prop-2-en-1-yl]-2,3-dihydro-1H-isoindol-1-one

HRID 70703
Notes
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Reaction equation

HRID 70703 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:27]2[NH:28][C:29](=[O:34])[C:30]([Cl:33])=[CH:31][CH:32]=2)=[CH:14]\[CH2:15][N:16]2[C:24](=O)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].O>CO>[C:3]([C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:27]2[NH:28][C:29](=[O:34])[C:30]([Cl:33])=[CH:31][CH:32]=2)=[CH:14]\[CH2:15][N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67399029HCID 67399029, compound

Product 1

HCID 584527122-[(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-oxo-1,6-dihydropyridin-2-yl)prop-2-en-1-yl]-2,3-dihydro-1H-isoindol-1-oneYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (52 mg) was added to a suspension of 2-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-oxo-1,6-dihydropyridin-2-yl)prop-2-en-1-yl]-1H-isoindole-1,3(2H)-dione (50 mg) in methanol (2 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. A solution of the resulting residue in trifluoroacetic acid (2 mL) was stirred under ice-cooling, during which sodium borohydride (50 mg) was added thereto. The mixture was stirred at room temperature for one hour. The reaction solution was ice-cooled, adjusted to a pH of 12 or more with a 1 M sodium hydroxide solution and then extracted with chloroform. The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) and then powdered with ethyl acetate. The precipitated crystals were collected by filtration and dried to give the title compound as a colorless powder (11 mg, 23%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. stirringA solution of the resulting residue in trifluoroacetic acid (2 mL) was stirred under ice-
  7. temperaturecooling, during which sodium borohydride (50 mg)
  8. additionwas added
  9. stirringThe mixture was stirred at room temperature for one hour
  10. temperaturecooled
  11. extractionextracted with chloroform
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. filtrationfiltered
  14. customThe solvent was then evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)
  16. filtrationThe precipitated crystals were collected by filtration
  17. customdried

Sources & evidence

ORD record
ord-38fe9129eebb47cdb5387b1a4790ec2e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes