Cesium carbonate → 4-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

HRID 12452

Reaktionsgleichung

Reaktionsgleichung von HRID 12452
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8](Br)=[C:9]([CH3:11])[N:10]=1)=[O:5])[CH3:2].[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:21]2[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[C:9]([CH3:11])[N:10]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 59338079Ethyl 5-bromo-4-methylthiazole-2-carboxylate

Produkt 1

HCID 593384494-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 5-bromo-4-methyl-thiazole-2-carboxylic acid ethyl ester (60 mg, 0.24 mmol) in 1,4-dioxane (2 ml) is added 1-naphthaleneboronic acid (50 mg, 0.29 mmol), cesium carbonate (187 mg, 0.58 mmol) and Pd(PPh3)4 (28 mg, 0.024 mmol). The reaction mixture is stirred in a sealed tube at 110° C. overnight. After cooling to rt, the mixture is purified by PTLC to give the title compound.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customthe mixture is purified by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-9f1c3eae5e914686a5941e976dd60d69
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728009B1

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