HCID 53703865, compound → HCID 53867839, compound

HRID 326097Notes

Reaction equation

HRID 326097 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]2[C:16]([C:20]3[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=3)=[N:17][CH2:18][CH2:19][C:7]=12)[CH3:2]>C1(OC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]2[C:16]([C:20]3[CH:21]=[CH:22][C:23]([S:26][CH3:27])=[CH:24][CH:25]=3)=[N:17][CH:18]=[CH:19][C:7]=12)[CH3:2]

Participants

4

Reactant 1

HCID 53703865HCID 53703865, compound

Product 1

HCID 53867839HCID 53867839, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 7583Diphenyl EtherSolvent

Procedure

2 g of 7-fluoro-1-(p-methylthio-phenyl)-3,4-dihydro-pyrimido[1,6-a]indole-5-acetic acid ethyl ester are heated under reflux, while stirring, in 20 ml of diphenyl ether with 0.5 g of palladium-on-carbon (10%). After 2 hours, a further 0.5 g of palladium-on-carbon is added and the mixture is heated for a further 3 hours. After filtering off the catalyst, the reaction mixture is concentrated in vacuo, the residue is taken up in a little ethyl acetate and chromatographed over silica gel. Using hexane/ethyl acetate (9:1) fractions are obtained which, after concentration by evaporation and recrystallization from ether, yield 7-fluoro-1-(p-methylthio-phenyl)pyrimido[1,6-a]indole-5-acetic acid ethyl ester having a melting point of 120°-122°. ##STR31## The following are obtained in an analogous manner:

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture is heated for a further 3 hours
  3. filtrationAfter filtering off the catalyst
  4. concentrationthe reaction mixture is concentrated in vacuo
  5. customchromatographed over silica gel
  6. customUsing hexane/ethyl acetate (9:1) fractions are obtained which
  7. concentrationafter concentration
  8. customby evaporation and recrystallization from ether

Sources & evidence

ORD record
ord-817985508802471b83e8baba79d98cc0
Source dataset
uspto-grants-1984_04
Patent number
US04444768

Reaction notes

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