Triethylamine → 3-(4-Chloro-phenyl)-6-trimethylsilanylethynyl-pyridazine

HRID 1916670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916670
C(N(CC)CC)C.[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])#[CH:9].Cl[C:15]1[N:16]=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1>C(#N)C.C1COCC1.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].[Cu]I>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[N:17]=[N:16][C:15]([C:9]#[C:8][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:20][CH:19]=2)=[CH:26][CH:25]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 122575023-Chloro-6-(4-chlorophenyl)pyridazine

Produkt 1

HCID 673622923-(4-Chloro-phenyl)-6-trimethylsilanylethynyl-pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an argon atmosphere 3.48 mL (25.0 mmol) triethylamine and 2.08 mL (15.0 mmol) ethynyl-trimethyl-silane are added successively to a solution of 2.25 g (10.0 mmol) 3-chloro-6-(4-chloro-phenyl)-pyridazine in 50 mL acetonitrile and 20 mL THF. Then 292 mg (0.40 mmol) Pd(dppf)Cl2 and 76 mg (0.40 mmol) CuI are added. The reaction solution is stirred overnight at RT. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (PE/EtOAc 1:1).

Aufarbeitung

  1. customand further purification

Quellen und Nachweise

ORD-Eintrag
ord-6769e4aee5d84ff38a3148d9f023d6eb
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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