Water → 5-Chloro-3-{4-[(5-chloropyridin-2-yl)oxy]phenyl}pyridin-2-amine

HRID 1405725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405725
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11](F)=[N:12][CH:13]=1.[NH2:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:20][C:19]([Cl:29])=[CH:18][N:17]=1.O>CS(C)=O>[Cl:29][C:19]1[CH:20]=[C:21]([C:22]2[CH:23]=[CH:24][C:25]([O:28][C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][N:12]=3)=[CH:26][CH:27]=2)[C:16]([NH2:15])=[N:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3458175-Chloro-2-fluoropyridineHCID 667480044-(2-Amino-5-chloropyridin-3-yl)phenol

Produkt 1

HCID 667487315-Chloro-3-{4-[(5-chloropyridin-2-yl)oxy]phenyl}pyridin-2-amineAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of potassium carbonate (376 mg), 5-chloro-2-fluoropyridine (215 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (300 mg) in DMSO (10 mL) was stirred at 120° C. for 5 hr. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (450 mg) as a pale yellow solid.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH aq. and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4fd3e9d0e31f4df1b6f93ff27d4bef42
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916551B2

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