Sodium Carbonate → 3-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amine

HRID 1747912

Reaktionsgleichung

Reaktionsgleichung von HRID 1747912
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[C:24]1[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][N:29]=1>O.COCCOC.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>[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:24]3[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][N:29]=3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 2762242-Amino-3-chloropyrazineHCID 222898184-Cyclohexyloxy-benzeneboronic acid

Produkt 1

HCID 667481483-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amineAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of sodium carbonate (491 mg), tetrakis(triphenylphosphine)palladium(0) (80 mg), 4-(cyclohexyloxy)phenylboronic acid (612 mg) and 3-chloropyrazin-2-amine (300 mg) in water (3 mL) and DME (15 mL) was stirred at 80° C. for 4 hr. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 3-[4-(cyclohexyloxy)phenyl]pyrazin-2-amine (485 mg) as a white solid.

Aufarbeitung

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d7412845e0a54ccda45222a923375a40
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150591B2

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