Toluene → 5-Phenyl-2-pyridinamine

HRID 1093684Notes

Reaction equation

HRID 1093684 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(B(O)O)C=CC=CC=1.[NH2:23][C:24]1[CH:29]=[CH:28]C(I)=[CH:26][N:25]=1>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.O>[C:1]1([C:7]2[CH:28]=[CH:29][C:24]([NH2:23])=[N:25][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 1050975-Phenyl-2-pyridinamineYield 41%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of toluene (80 mL) and water (20 mL) was degassed with argon for 5 minutes. Sodium carbonate (9.63 g, 0.0909 mole) was added and the mixture was degassed with argon for 5 minutes. Phenylboronic acid (6.65 g, 0.05454 mole) and 2-amino-5-iodo-pyridine (10.0 g, 0.04545 mole) were then added and the mixture was degassed with argon for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (5.252 g, 0.00454 mole) was added was degassed with argon for 5 minutes. The resulting mixture was then heated to reflux for 3 hours. The mixture was diluted with ethyl acetate, and the organic layer was washed with water followed by brine solution. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography using silica gel 60-120 mesh (1% methanol in chloroform) afforded 3.2 g (41%) of 5-phenyl-pyridin-2-ylamine. LC-MS purity: 171.08 (M+1)+, 87%.

Workup

  1. customwas degassed with argon for 5 minutes
  2. customthe mixture was degassed with argon for 5 minutes
  3. customthe mixture was degassed with argon for 5 minutes
  4. customwas degassed with argon for 5 minutes
  5. temperatureThe resulting mixture was then heated
  6. temperatureto reflux for 3 hours
  7. additionThe mixture was diluted with ethyl acetate
  8. washthe organic layer was washed with water
  9. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customPurification by column chromatography

Sources & evidence

ORD record
ord-0ba56c0c487e4b63bb734fd42806b2f5
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

Loading…