Tributylphosphine → 5-ethyl-8-nitro-5H-phenanthridin-6-one

HRID 968288Notes

Reaction equation

HRID 968288 reaction equation
C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(P(CCCC)CCCC)CCC.[CH2:43]([N:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:46](=[O:57])[C:47]1[CH:52]=[C:51]([N+:53]([O-:55])=[O:54])[CH:50]=[CH:49][C:48]=1Br)[CH3:44]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:43]([N:45]1[C:46](=[O:57])[C:47]2[C:48](=[CH:49][CH:50]=[C:51]([N+:53]([O-:55])=[O:54])[CH:52]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:58]1=2)[CH3:44]

Participants

7

Reactant 3

HCID 13831TributylphosphineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 22288552N-ethyl-2-bromo-5-nitro-N-phenyl-benzamide

Product 1

HCID 222885455-ethyl-8-nitro-5H-phenanthridin-6-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Palladium acetate (129 mg, 0.57 mmol) was added to a suspension of silver carbonate (1.6 g, 5.72 mmol), 1,3-bis(diphenylphosphino)propane (236 mg, 0.57 mmol), tributylphosphine (0.713 ml, 579 mg, 2.86 mmol) and N-ethyl-2-bromo-5-nitro-N-phenyl-benzamide (1.0 g, 2.86 mmol) in DMF (15 ml). The reaction mixture was heated to reflux for 30 minutes and cooled to 23° C. The mixture was filtered through a plug of celite, and the filter cake was washed with ethyl acetate (50 ml). The combined filtrates were washed with saturated sodium chloride (3-30 ml portion), dried over anhydrous sodium sulfate, and were concentrated. The residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane) afforded 5-ethyl-8-nitro-5H-phenanthridin-6-one I-16b (111 mg, 14%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe mixture was filtered through a plug of celite
  4. washthe filter cake was washed with ethyl acetate (50 ml)
  5. washThe combined filtrates were washed with saturated sodium chloride (3-30 ml portion)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationwere concentrated
  8. customThe residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-6589a8992bb5451d94025660954e41c7
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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