Potassium Carbonate → 3-(4-Methyl-2-nitro-phenyl)-pyridine

HRID 227235

Reaction equation

HRID 227235 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.[C:21](=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][C:2]1[CH:7]=[CH:6][C:5]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenolHCID 27343783-Pyridinylboronic acid

Product 1

HCID 117459723-(4-Methyl-2-nitro-phenyl)-pyridine

Reagents, catalysts & solvents 5

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

4-Bromo-2-nitro-phenol (648 mg, 3.0 mmol) and 3-pyridyl boronic acid (387 mg, 3.15 mmol) were diluted with 5 mL of dioxane and placed under N2. Potassium carbonate was diluted in 1 mL of H2O and added to the reaction mixture. Tetrakis(triphenylphosphine) palladium (173 mg, 0.15 mmol) was added, then the reaction was heated to 70° C. and stirred overnight. The reaction was allowed to cool to room temperature, then diluted with 30 mL of EtOAc and 30 mL of 10% Na2CO3. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The material was purified with a Biotage 40M cartridge eluting with hexanes/EtOAc, 1/1 to yield an off white solid.

Workup

  1. additionadded to the reaction mixture
  2. temperatureto cool to room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was purified with a Biotage 40M cartridge
  8. washeluting with hexanes/EtOAc, 1/1
  9. customto yield an off white solid

Sources & evidence

ORD record
ord-1cd7e63882694d8b92fa652bbf8ab09d
Source dataset
uspto-grants-2009_07
Patent number
US07560462B2

Linked notes

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