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Isobutylene oxide → 1-[5-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]-2-methylpropan-2-ol

HRID 385974
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 385974
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[N:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1.[O:14]1[C:16]([CH3:18])([CH3:17])[CH2:15]1.CC([O-])(C)C.[K+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]([CH2:15][C:16]([CH3:18])([OH:14])[CH3:17])[N:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11208Isobutylene oxideHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 1784328616-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine

Produkt 1

HCID 595262551-[5-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]-2-methylpropan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine (131 mg, 0.68 mmol) and 1,2-epoxy-2-methylpropane (65 μl, 0.71 mmol) were taken-up in DMF (2.7 ml). Potassium 2-methylpropan-2-olate (114 mg, 1.01 mmol) was added, and the mixture was heated to 60° C. for seven hours. Saturated aqueous ammonium chloride was added and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated, purified by reverse-phase HPLC (10-100% acetonitrile/water with 0.05% trifluoroacetic acid modifier). The appropriate fractions were neutralized with aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound.

Aufarbeitung

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (10-100% acetonitrile/water with 0.05% trifluoroacetic acid modifier)
  6. extractionextracted twice with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8e16de72a4f94da390416b37e42a2ce7
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367706B2

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