Acetonitrile → HCID 18331442, compound

HRID 2270553Notes

Reaction equation

HRID 2270553 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[CH:10][N:9]=1.[C:20](#[N:22])[CH3:21]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[NH2:22][CH2:20][C:21]1[CH:8]=[C:13]([NH:14][C:8]2[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[CH:10][N:9]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 757382-Chloro-3,5-dinitropyridine

Product 1

HCID 18331442HCID 18331442, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)Catalyst

Conditions

Temperature
80 °C

Procedure

A mixture of the thus obtained resin (100 mg, 0.071 mol), potassium carbonate (100 mg), 2-chloro-3,5-dinitropyridine (72 mg), palladium (II) acetate (16 mg), diphenylphosphinoferrocene (79 mg) and acetonitrile (9 ml) was stirred under a nitrogen atmosphere at 80° C. and then filtered. The resulting resin was washed sequentially with dimethylformamide, water, methanol and methylene chloride, dried under reduced pressure and, after adding trifluoroacetic acid, the mixture was stirred at room temperature for 1 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the resulting residue, water and ethyl acetate were added. The aqueous layer was washed with ethyl acetate and concentrated under reduced pressure. The resulting residue was purified with Sep-PaK® Plus C18 Cartridges (Waters) to give 1.7 mg of the titled compound (8%).

Workup

  1. filtrationfiltered
  2. washThe resulting resin was washed sequentially with dimethylformamide, water, methanol and methylene chloride
  3. customdried under reduced pressure
  4. additionafter adding trifluoroacetic acid
  5. stirringthe mixture was stirred at room temperature for 1 h
  6. filtrationThe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionTo the resulting residue, water and ethyl acetate were added
  9. washThe aqueous layer was washed with ethyl acetate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified with Sep-PaK®

Sources & evidence

ORD record
ord-6d4a784a96c54d70928fe97902fcf562
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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