Sodium Carbonate → [2,3'-Bipyridin]-6-amine

HRID 852901

Reaktionsgleichung

Reaktionsgleichung von HRID 852901
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.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:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:7]1[CH:2]=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 3008092-Amino-6-bromopyridine

Produkt 1

HCID 11586359[2,3'-Bipyridin]-6-amineAusbeute 153,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred degassed suspension of a mixture of 2-amino-6-bromopyridine (5.38 g, 31.09 mmol), 2,4,6-(3-pyridinyl)-cyclotriboroxane (3.80 g, 12.07 mmol) and aqueous Na2CO3 (100 mL, 0.4M) in acetonitrile (100 mL) at room temperature Pd(PPh3)4 (1.70 g, 1.47 mmol) was added. The reaction mixture was heated at 95° for 1 to 2 days under nitrogen, cooled to the room temperature and filtered. The filtrate was concentrated purified by flash chromatography on silica gel (MeOH/CH2Cl2: 5/95→10/90 plus a few drops of NH4OH) and co-precipitated with a mixture of AcOEt/CH2Cl2/hexane to afford the title compound 11 (4.091 g, 23.90 mmol, 77% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.16 (dd, J=2.2, 0.8 Hz, 1H), 8.57 (dd, J=4.7, 1.6 Hz, 1H), 8.33-8.28 (m, 1H), 7.54-7.44 (m, 2H), 7.14 (dd, J=7.3, 0.5 Hz, 1H), 6.49 (dd, J=8.2, 0.4 Hz, 1H), 6.12 (bs, 2H).

Aufarbeitung

  1. customTo a stirred degassed
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 95° for 1 to 2 days under nitrogen
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography on silica gel (MeOH/CH2Cl2: 5/95→10/90 plus a few drops of NH4OH) and co-precipitated with a mixture of AcOEt/CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f3cdb8976bc24d609d09638526a5faaf
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253204B2

Verknüpfte Notizen

Wird geladen…