Sodium Carbonate → 4-Chloro-3-(4-phenoxyphenyl)pyridin-2-amine

HRID 1405886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405886
C(=O)([O-])[O-].[Na+].[Na+].[O:7]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[C:25]=1I>COCCOC.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>[Cl:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[C:25]=1[C:17]1[CH:18]=[CH:19][C:14]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:15][CH:16]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 229365964-Chloro-3-iodopyridin-2-amine

Produkt 1

HCID 667485774-Chloro-3-(4-phenoxyphenyl)pyridin-2-amineAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of sodium carbonate (122 mg), tetrakis(triphenylphosphine)palladium(0) (33.2 mg), 4-phenoxyphenylboronic acid (160 mg) and 4-chloro-3-iodopyridin-2-amine (146 mg) in DME (10 mL) and water (3 mL) was stirred at 80° C. overnight. The mixture was added with silica gel, concentrated in vacuo, and purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (111 mg) as a pale yellow solid.

Aufarbeitung

  1. additionThe mixture was added with silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-73c9e0d84c4140c5847e480ce4224dfb
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916551B2

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