Nitrogen → HCID 86690310, Verbindung

HRID 1428658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428658
Br[C:2]1[C:3]([NH2:22])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.N#N.C(N(CC)CC)C.[C:32]([CH:34]1[CH2:36][CH2:35]1)#[CH:33]>O1CCOCC1.[Cu]I.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>[CH:34]1([C:32]#[C:33][C:2]2[C:3]([NH2:22])=[N:4][C:5]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[N:7]=2)[CH2:36][CH2:35]1

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 86690308HCID 86690308, Verbindung

Produkt 1

HCID 86690310HCID 86690310, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418807HCID 178418807, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-5,6-di-p-tolylpyrazin-2-amine (step 3) (440 mg, 1.24 mmol) in dioxane (5 ml) was degassed with N2 and treated with triethylamine (1.558 ml, 11.18 mmol), ethynylcyclopropane (0.210 ml, 2.484 mmol), copper(I) iodide (71.0 mg, 0.373 mmol) and PdCl2(dppf)-CH2Cl2-adduct (101 mg, 0.124 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated under reduced pressure and dry loaded onto silica using DCM (10 ml). Purification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane afforded the titled compound as a beige coloured solid;

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customdry
  3. customPurification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-60b4257538a64b26afb97605116f8892
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937069B2

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