Sodium Carbonate → 2-(2-Fluorophenyl)-5-nitropyridine

HRID 1931432Notes

Reaction equation

HRID 1931432 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 782402-Bromo-5-nitropyridineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 685377752-(2-Fluorophenyl)-5-nitropyridine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

5 g (24.6 mmol) of 2-bromo-5-nitro-pyridine, 3.79 g (27.1 mmol) of 2-fluoro-phenylboronic acid, 276.5 mg (1.23 mmol) of palladium acetate, 646 mg (2.46 mmol) of triphenylphosphine and 24.6 ml of a 1 M aqueous sodium carbonate solution in 150 ml of toluene and 37 ml of ethanol were heated under reflux for 5 h. After cooling, the mixture concentrated under reduced pressure to half of its volume, poured onto water and extracted with ethyl acetate. The combined organic phases were dried and evaporated. The product was purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 4.2 g.

Workup

  1. temperatureunder reflux for 5 h
  2. temperatureAfter cooling
  3. concentrationthe mixture concentrated under reduced pressure to half of its volume
  4. additionpoured onto water
  5. extractionextracted with ethyl acetate
  6. customThe combined organic phases were dried
  7. customevaporated
  8. customThe product was purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-229beb32bea84fcba3cbd3db11df6b16
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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