Potassium Carbonate → 2-[4-(3-Methanesulfonyl-propoxy)-2,6-dimethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester

HRID 2272826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272826
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=3[CH3:22])[N:13]=2)[CH:10]=1)=[O:4].[CH3:23][S:24]([CH2:27][CH2:28][CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([C:14]3[C:15]([CH3:22])=[CH:16][C:17]([O:21][CH2:29][CH2:28][CH2:27][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:18][C:19]=3[CH3:20])[N:13]=2)[CH:10]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonateHCID 136992563Methyl 2-(4-hydroxy-2,6-dimethylphenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylate

Produkt 1

HCID 1181299702-[4-(3-Methanesulfonyl-propoxy)-2,6-dimethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl esterAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-(4-hydroxy-2,6-dimethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester (0.2 g, 0.673 mmol) in acetonitrile (5 mL) is added toluene-4-sulfonic acid 3-methanesulfonyl-propyl ester (0.196 g, 0.673 mmol) and potassium carbonate (0.278 g, 2.019 mmol) at room temperature and the reaction mixture is heated at 100° C. for 16 hours. The reaction mixture is diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts are washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered, and evaporated to dryness. The crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column) and is eluted with 40-60% EtOAc in hexane to give the title compound as a light yellow solid (198 mg, 70%). LCMS m/z 418 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts are washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column)
  7. washis eluted with 40-60% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-7890c147dc31499ab2d4ae37c5ea1c02
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120793B2

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