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

HRID 1767609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767609
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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 4595173-(2-Pyridyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a6420ce983a8419ca6a9dc7af2f929c8
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235548B2

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