tert-Butanol → tert-butyl N-(4-bromo-1-methyl-1H-pyrazol-5-yl)carbamate

HRID 919085

Reaktionsgleichung

Reaktionsgleichung von HRID 919085
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1C(O)=O.C([N:13]([CH2:16]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>C1(C)C=CC=CC=1>[C:35]([O:39][C:16](=[O:25])[NH:13][C:3]1[N:4]([CH3:7])[N:5]=[CH:6][C:2]=1[Br:1])([CH3:38])([CH3:37])[CH3:36]

Komponenten

6

Edukt 4

HCID 6386tert-Butanol2×HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6736864-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid

Produkt 1

HCID 67957972tert-butyl N-(4-bromo-1-methyl-1H-pyrazol-5-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Bromo-2-methyl-2H-pyrazole-3-carboxylic acid (2 g, 9.76 mmol) and triethylamine (1.50 mL, 10.73 mmol) were combined in toluene (10 mL). Diphenylphosphoryl azide (2.31 mL, 10.73 mmol) was added and the reaction stirred at room temperature for 3 hours. tert-Butanol (1.12 mL, 11.71 mmol) was added and the reaction was stirred at 60° C. overnight. After cooling the t-BuOH was removed under vacuum and the reaction was submitted to EtOAc/H2O workup. The crude material was purified via silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. stirringthe reaction was stirred at 60° C. overnight
  2. customwas removed under vacuum
  3. customThe crude material was purified via silica gel chromatography (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-42ab1a38aafa4a9999ebc7f8487eebf0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09272990B2

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