2-Bromopyridine → 3-(2-Pyridyl)aniline

HRID 1592813Notes

Reaction equation

HRID 1592813 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:13]1[CH:14]=[C:9]([NH2:8])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acid

Product 1

HCID 4595173-(2-Pyridyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromopyridine (2.00 mL), 3-aminophenylboronic acid (5.40 g) and palladium tetrakistriphenylphosphine (1.2512 g) were added to a mixture of 130 mL of dimethoxyethane and 32 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90° C. overnight. The reaction mixture was then cooled to room temperature and diluted with water (300 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 2.75 g of 3-(pyridin-2-yl)benzenamine.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customair-dried
  5. customThe dried material was purified

Sources & evidence

ORD record
ord-39e96961775443cdbee15c8db22d57cd
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

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