1,2-Dimethoxyethane → 2-Amino-3,5-diphenylpyridine

HRID 251777Notes

Reaction equation

HRID 251777 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CO[CH2:21][CH2:22]OC.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.C(OCC)(=O)C>[C:10]1([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:22]3[CH:21]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:6]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 988513,5-Dibromo-2-pyridylamine

Product 1

HCID 115723272-Amino-3,5-diphenylpyridine

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolving 5.0 g (20 mmol) of 2-amino-3,5-dibromo pyridine, 5.0 g (41 mmol) of phenylboronic acid and 0.92 g of tetrakis (triphenylphosphine) palladium into 130 milliliter of 1,2-dimethoxyethane, adding 62 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the resultant solution was further dissolved into ethyl acetate, filtering the solution, washing with water, dried with the use of sodium sulfate. Removing the solvent by distillation, 8.9 g of crude 3,5-diphenyl-2-amino-pyridine was obtained.

Workup

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

Sources & evidence

ORD record
ord-960ae32376574d9c91ce4c340557126e
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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