Sodium Carbonate → 4-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol

HRID 1766740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766740
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:19](=[O:22])([O-])[O-].[Na+].[Na+]>COCCOC.O.C(OCC)(=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:3]2[CH:4]=[CH:5][C:19]([OH:22])=[CH:7][CH:2]=2)=[CH:3][C:4]=1[O:9][CH2:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18]

Komponenten

7

Edukt 2

HCID 10340Sodium CarbonateHCID 211114873-(2,6-Dichlorobenzyloxy)-5-bromopyridin-2-amine

Produkt 1

HCID 104286454-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3-(2,6-dichloro-benzyloxy)-pyridin-2-ylamine (example I(a), 100 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3-2-dioxabordan-2-yl) phenol (86 mg, 0.35 mmol), bis(triphenylphosphine) palladium(II) chloride (8 mg, 0.009 mmol) and sodium carbonate (91 mg, 0.87 mmol) in ethylene glycol dimethyl ether (10 mL) and water (0.5 mL) was heated to reflux under nitrogen for 18 hours. The reaction was cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water, brine, dried over Na2SO4, and purified on silica column to afford 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol as light pine crystals (89 mg, 85% yield).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 18 hours
  3. washThe mixture was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. custompurified on silica column

Quellen und Nachweise

ORD-Eintrag
ord-8189ddcbb8ef4a73b0e60e47a1d014ee
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230098B2

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