4-[(2-Fluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinone → 6-Fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one

HRID 2081198Notes

Reaction equation

HRID 2081198 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH2:14][CH2:13][NH:12][C:11](=[O:15])[CH:10]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[C:3]2[NH:8][C:9]3[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:10]=3[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 157124944-[(2-Fluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinone

Product 1

HCID 157124986-Fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-oneYield 155.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Cupric acetate (2.71 g) was added to a stirred solution of 4-[(2-fluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinone (1.4 g) and palladium (II) acetate (280 mg) in dry DMF (28 ml) under nitrogen. The mixture was heated at 130° for 1.5 h and the solvent was removed in vacuo. The residue was treated with hot methanol (50 ml) and the suspension was filtered and washed with hot methanol (3×50 ml). The combined filtrates were evaporated to give a gum (2.16 g) which was purified by FCC eluting with System A (200:10:1) to give the title compound (490 mg), m.p. 255°-257°.

Workup

  1. temperatureThe mixture was heated at 130° for 1.5 h
  2. customthe solvent was removed in vacuo
  3. additionThe residue was treated with hot methanol (50 ml)
  4. filtrationthe suspension was filtered
  5. washwashed with hot methanol (3×50 ml)
  6. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-1ad2eaad8e8a4d94814ac0d5867629a9
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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