Cesium carbonate → 4-(Pyridin-4-yl)aniline

HRID 2244976Notes

Reaction equation

HRID 2244976 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.Cl.Br[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=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:22]1[CH:23]=[CH:24][C:19]([C:9]2[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=2)=[CH:20][CH:21]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 881004-Bromopyridinium chlorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 15126544-(Pyridin-4-yl)anilineYield 78.8%

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 (1.33 g, 6.07 mmol) in toluene (20 mL) and n-butanol (7 mL), a solution of 4-bromopyridine hydrochloride (0.608 g, 3.13 mmol) and Cs2CO3 (3.0-6 g, 9.39 mmol) in H2O (15 mL) was added. The mixture was degassed three times with Ar/vacuum cycle before being charged with Pd(Ph3P)4 (0.270 g, 0.230 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 (0.420 g). MS 171.0 (M+H)

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-0cf98432cd4244a0bb70d2617c6558ab
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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