Dimethyl Sulfoxide → Methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate

HRID 1845286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845286
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CCOC(C)=O>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([O:1][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 58188160Methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate

Produkt 1

HCID 58188068Methyl 3-(5-methylpyridin-2-yl)-5-(thiazol-2-yloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A stirred mixture of methyl 3-hydroxy-5-(5-methylpyridin-2-yl)benzoate (290 mg, 1.2 mmol), 2-bromothiazole (410 mg, 2.5 mmol), potassium carbonate (346 mg, 2.5 mmol), and dimethyl sulfoxide (5 mL) was heated at 135° C. overnight. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-30% EtOAc/hexane) to afford the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washThe organic phase was washed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d700671e81e34b619b4d8adaff40496d
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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