Sodium Carbonate → 2-Amino-6-phenylpyridine

HRID 1513621Notes

Reaction equation

HRID 1513621 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[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+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 5984302-Amino-6-phenylpyridineYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Amino-6-bromopyridine 10 g (58 mmol), phenylboronic acid 8.5 g (70 mmol) and tetrakis(triphenylphosphine)palladium 1.3 g (1.2 mmol) were dissolved in 60 mL of 1,2-dimethoxyethane. A 2.0M sodium carbonate aqueous solution 30 mL was added thereto, and the solution was refluxed for 8 hours under argon atmosphere by heating. After finishing the reaction, the aqueous layer was removed. The organic layer was dried on anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was refined by silica gel chromatography to obtain 6.9 g (yield: 70%) of 2-amino-6-phenylpyridine.

Workup

  1. temperaturethe solution was refluxed for 8 hours under argon atmosphere
  2. temperatureby heating
  3. customthe reaction
  4. customthe aqueous layer was removed
  5. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-183f8a871c2f4922b7fc4f5f99a4c18a
Source dataset
uspto-grants-2012_07
Patent number
US08217570B2

Reaction notes

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