Water → ethyl 5-(1-methyl-1H-pyrazol-4-yl)-1,3-thiazole-4-carboxylate

HRID 383928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383928
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][N:13]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[N:14]1.C([O-])([O-])=O.[Na+].[Na+].O>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>[CH3:12][N:13]1[CH:17]=[C:16]([C:2]2[S:6][CH:5]=[N:4][C:3]=2[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:15]=[N:14]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 12361218Ethyl 5-bromo-1,3-thiazole-4-carboxylate

Produkt 1

HCID 59291587ethyl 5-(1-methyl-1H-pyrazol-4-yl)-1,3-thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of ethyl 5-bromothiazole-4-carboxylate, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and Pd(PPh3)4 in dioxane was added a 2 M aqueous Na2CO3 solution, followed by heating under reflux for 4 hours. To the reaction mixture was added water and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:EtOAc) to obtain ethyl 5-(1-methyl-1H-pyrazol-4-yl)-1,3-thiazole-4-carboxylate as a brown solid.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-366e1cfd058445c7b7f48cb858488038
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367696B2

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