Triethylamine → HCID 178474492, Verbindung

HRID 588585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588585
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.I[C:17]1[C:18]([C:26]([F:29])([F:28])[F:27])=[N:19][NH:20][C:21]=1[NH:22][C:23](=[O:25])[CH3:24]>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([C:7]#[C:8][C:17]2[C:18]([C:26]([F:28])([F:29])[F:27])=[N:19][NH:20][C:21]=2[NH:22][C:23](=[O:25])[CH3:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 178474493HCID 178474493, Verbindung

Produkt 1

HCID 178474492HCID 178474492, VerbindungAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A degassed solution of phenylacetylene (3.9 ml, 35 mmol) and Et3N (36 mL) in DMF (13.5 mL) was added to N-[4-iodo-3-(trifluoromethyl)-1H-pyrazol-5-yl]acetamide (4.5 g, 14 mmol), CuI (530 mg, 2.8 mmol) and PdCl2(PPh3)2 (980 mg, 1.4 mmol) under an atmosphere of N2. The reaction was then heated to 85° C. for 3.5 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:9 to 1:0) yielding the title compound as a brown oil (3 g) which was used in the subsequent step.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:9 to 1:0)

Quellen und Nachweise

ORD-Eintrag
ord-610dd52908984e65a4a87b2bde01cdf0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227976B2

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