2-Bromopyridine → 4-(Pyridin-2-yl)aniline

HRID 1432539Notes

Reaction equation

HRID 1432539 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(O)CCC.O.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>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:9]1[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=1

Participants

8

Reactant 3

HCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 4595184-(Pyridin-2-yl)anilineYield 78.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 2631-ButanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.66 g, 12.1 mmol) in toluene (20 mL) and n-butanol (7 mL), a solution of 2-bromopyridine (0.991 g, 6.27 mmol) and Cs2CO3 (6.10 g, 18.7 mmol) in H2O (20 mL) was added. The mixture was degassed three times with Ar/vacuum cycle before being charged with Pd(Ph3P)4 (540 mg, 0.46 mmol, 7% mol). It was then heated at reflux under Ar overnight. The reaction mixture was allowed to cool at room temperature, and then in an ice-bath. The precipitates were collected, dried on vacuum to give a solid (0.840 g)

Workup

  1. customThe mixture was degassed three times with Ar/vacuum cycle
  2. temperatureIt was then heated
  3. temperatureat reflux under Ar overnight
  4. customThe precipitates were collected
  5. customdried on vacuum

Sources & evidence

ORD record
ord-85d3d8cb76284b46b2a26f4cf99e789b
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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