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

HRID 496099Notes

Reaction equation

HRID 496099 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][CH:12]=1.[NH2:16][C:17]1C=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.BrC1C=CC=CN=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:16]1[CH:17]=[CH:22][CH:21]=[CH:20][C:19]=1[C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[NH2:6]

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 162111393-Aminophenylboronic Acid Hemisulfate

Product 1

HCID 4595173-(2-Pyridyl)aniline

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Aminophenylboronic acid hemisulphate (5.58 g, 30 mmol), 2-bromopyridine (2.7 ml, 28 mmol), Pd(PPh3)2Cl2 (100 mg, 0.5 mol %), 2M K2CO3 (50 ml) were refluxed in 1,2-dimethoxyethane (50 ml) for 24 h under N2. The mixture was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3 (50 ml). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure. Flash-chromatography with CH2Cl2 as eluent gave 3-(2-pyridyl)aniline as a yellow oil, 1.0 g (21%). 3-(2-Pyridyl)aniline was transformed by Method B and Method G (using cyclohexanecarboxaldehyde). M.p. 213-216° C.

Workup

  1. washwashed with sat. NaHCO3 (50 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2687b25969334e55848d52873f0487bc
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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