Water → Ethyl 4-methyl-2-(4-nitrophenyl)thiazole-5-carboxylate

HRID 43565

Reaktionsgleichung

Reaktionsgleichung von HRID 43565
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[C:14]1[S:15][C:16]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:17]([CH3:19])[N:18]=1.C(=O)(O)[O-].[Na+].O>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.O1CCOCC1>[CH3:19][C:17]1[N:18]=[C:14]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[S:15][C:16]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Komponenten

7

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 3824379Ethyl 4-methyl-2-(4-nitrophenyl)thiazole-5-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The same operation as in Example (91a) was performed using 4-nitrophenylboronic acid (1 g, 6 mmol), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (1 g, 4 mmol), sodium bicarbonate (1.34 g, 16 mmol), tetrakis(triphenylphosphine)palladium (460 mg, 0.4 mmol), water (5 mL) and 1,4-dioxane (10 mL), to obtain 0.97 g of the title compound as a light yellow solid (83%).

Quellen und Nachweise

ORD-Eintrag
ord-8b2a1695f7b54d71879ca5e567aac508
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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