Nitrogen → HCID 86690309, Verbindung

HRID 1521918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521918
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1I.N#N.B(O)(O)[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[C:16]1([CH3:19])[CH:15]=[CH:14][C:13]([C:3]2[N:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 59457651HCID 59457651, Verbindung

Produkt 1

HCID 86690309HCID 86690309, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of 6-chloro-5-iodopyrazin-2-amine (step 1) (13.74 g, 53.8 mmol) in dioxane (300 ml) was degassed with N2 and treated with p-tolylboronic acid (17.55 g, 129 mmol), K2CO3 (22.30 g, 161 mmol) and PdCl2(dppf)-CH2Cl2-adduct (4.39 g, 5.38 mmol). The orange suspension was stirred at 110° C. for 2 days. After cooling to room temperature the reaction mixture was concentrated under reduced pressure. The crude mixture was absorbed onto silica and purification by chromatography eluting with 0-60% EtOAc in iso-hexane afforded the titled compound as a beige coloured solid;

Aufarbeitung

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe crude mixture was absorbed onto silica and purification by chromatography
  4. washeluting with 0-60% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-dbb7b88f0b68436eba366b513cd829bc
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073932B2

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