HCID 19799249, compound → HCID 19799247, compound

HRID 2081199Notes

Reaction equation

HRID 2081199 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH2:14][CH2:13][NH:12][C:11](=[O:15])[CH:10]=2)=[CH:4][CH:3]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:10]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 19799249HCID 19799249, compound

Product 1

HCID 19799247HCID 19799247, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Cupric acetate (2.9 g) was added to a stirred solution of 4-[(4-fluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinone (1.5 g) and palladium (II) acetate (200 mg) in dry DMF (40 ml). The mixture was heated at 130° for 1 h, evaporated in vacuo and the residue was extracted with methanol (250 ml). This solution was concentrated in vacuo and the residue was purified by FCC eluting with System A (100:8:1) to give the title compound (840 mg), m.p. 242°-245°.

Workup

  1. temperatureThe mixture was heated at 130° for 1 h
  2. customevaporated in vacuo
  3. extractionthe residue was extracted with methanol (250 ml)
  4. concentrationThis solution was concentrated in vacuo
  5. customthe residue was purified by FCC
  6. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-8ff7208c861c427faf04baef27141861
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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