Sodium Carbonate → 2-(2-Aminopyridin-4-yl)-4-chlorophenol

HRID 46362

Reaktionsgleichung

Reaktionsgleichung von HRID 46362
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](B(O)O)[CH:7]=1.[NH2:12][C:13]1[CH:18]=[C:17](Br)[CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(OCC)(=O)C.O.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>[NH2:12][C:13]1[CH:18]=[C:17]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[OH:11])[CH:16]=[CH:15][N:14]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 6932822-Amino-4-bromopyridineHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 1360636192-(2-Aminopyridin-4-yl)-4-chlorophenolAusbeute 109,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

5-chloro-2-hydroxyphenylboronic acid (200 mg, 1 mmol), 2-amino-4-bromopyridine (220 mg, 1.3 mmol), sodium carbonate (490 mg, 4.6 mmol), and tetrakis(triphenylphosphine)palladium (0) (130 mg, 0.12 mmol) were all placed in a round bottom flask and 1,4-dioxane (3 mL) and water (1 mL) were added. The mixture was heated to 85° C. for 2 hours. The mixture was cooled to room temperature and diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate (1×). The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (12 g silica gel column, 0-100% v/v ethyl acetate/hexanes gradient elution) to afford the title compound (242 mg).

Aufarbeitung

  1. customall placed in a round bottom flask
  2. temperatureThe mixture was cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (1×)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (12 g silica gel column, 0-100% v/v ethyl acetate/hexanes gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-304f70f0a6b34a218d0d0242ec2fd6cb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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