4-Bromo-2-nitroaniline → HCID 10353230, Verbindung

HRID 730233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730233
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)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+:18]([C:13]1[CH:12]=[C:11]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:16]=[CH:15][C:14]=1[NH2:17])([O-:20])=[O:19]

Komponenten

7

Edukt 2

HCID 701324-Bromo-2-nitroanilineHCID 2734379(Pyridin-4-yl)boronic acid

Produkt 1

HCID 10353230HCID 10353230, VerbindungAusbeute 119,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

To a mixture of pyridine-4-boronic acid (3 mmol), 4-bromo-2-nitrophenylamine (2 mmol), and Pd(PPh3)4 (20 mg) in DME (10 mL), 2 M aqueous Na2CO3 was added. The suspension was then refluxed under nitrogen for 36 h. After cooling to the room temperature, the reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with brine (50 mL), dried over sodium sulfate, and concentrated under vacuum. The residue obtained was purified by column chromatography eluting with hexanes/ethyl acetate (1:1) then ethyl acetate/methanol (10:1) to give 516 mg of 2-nitro-4-pyridin-4-ylphenylamine. 1H NMR (DMSO-d6, 400 MHz): LC: Tr 0.44 min, MS: 216.1 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 7.13 (d, 1H), 7.60 (d, 2H), 7.69 (bs, 2H), 7.88 (dd, 1H), 8.37 (d, 1H), 8.55 (d, 2H) ppm.

Aufarbeitung

  1. additionwas added
  2. temperatureThe suspension was then refluxed under nitrogen for 36 h
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customwas purified by column chromatography
  8. washeluting with hexanes/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-71a4331336504c27b746f1b401715061
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582673B2

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