Potassium Carbonate → 3-Fluoro-4-(4-nitrophenyl)pyridine

HRID 1510236Notes

Reaction equation

HRID 1510236 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[F:20].C(=O)([O-])[O-].[K+].[K+]>COCCOC.[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>[F:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 38524294-Chloro-3-fluoropyridine

Product 1

HCID 690819133-Fluoro-4-(4-nitrophenyl)pyridineYield 121.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of (4-nitrophenyl)boronic acid (1.6 g), 4-chloro-3fluoropyridine (1.11 g), and tetrakis (triphenylphosphine) palladium (462 mg) in 1,2-dimethoxyethane (25 mL) was added 0.8M potassium carbonate aqueous solution (25 mL) and the mixture was refluxed under nitrogen for 20 hours. After cooling, 1,2-dimethoxyethane was removed in vacuo. To the residue was added ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated to afford 3-fluoro-4-(4-nitrophenyl)pyridine (2.23 g) as a brown solid.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 20 hours
  2. temperatureAfter cooling
  3. custom1,2-dimethoxyethane was removed in vacuo
  4. additionTo the residue was added ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-25b1b8d2d2f44db99655671ef6d616ea
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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