Sodium Carbonate → 5-Phenyl-2-pyridinamine

HRID 251779

Reaction equation

HRID 251779 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.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.COCCOC>[C:9]1([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 706222-Amino-5-bromopyridine

Product 1

HCID 1050975-Phenyl-2-pyridinamineYield 113.8%

Reagents, catalysts & solvents 2

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

Procedure

Dissolving 5.5 g (32 mmol) of 2-amino-5-bromopyridine, 4.3 g (32 mmol) of phenylboronic acid and 0.80 g of tetrakis (triphenylphosphine) palladium into 100 milliliter of 1,2-dimethoxyethane, adding 50 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 8 hours. After completion of the reaction and after filtration of the solution, washing the organic layer with water, dried it with the use of sodium sulfate. Removing the solvent by distillation, 6.2 g of crude 5-phenyl-2-amino-pyridine was obtained.

Workup

  1. temperatureunder heating for 8 hours
  2. customAfter completion of the reaction
  3. filtrationafter filtration of the solution
  4. washwashing the organic layer with water
  5. dry with materialdried it with the use of sodium sulfate
  6. customRemoving the solvent
  7. distillationby distillation

Sources & evidence

ORD record
ord-ec9a1cc466e646a2a696f9652a37ef15
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Linked notes

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