Reaktion #417952

ord-84aa7a522d6045189b35bc87ee1144ae

Reaktionsgleichung

CS(C)(=O)=O
dimethyl sulfone
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium-bis-(trimethylsilyl)-amide
C1CCOC1
THF
Fc1cccc(Br)n1
2-bromo-6-fluoropyridine
CS(=O)(=O)C1(c2cccc(Br)n2)CC1
2-Bromo-6-(1-methanesulfonyl-cyclopropyl)-pyridine

Reaktionsbedingungen

Temperatur
-17°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction is quenched by the addition
  2. 2
    ExtraktionNaCl solution and extracted with EtOAc
  3. 3
    TrocknenThe organic layer is dried over MgSO4
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigethe solvent is removed in vacuo

Vorschrift

Under inert gas atmosphere 28.4 mL (56.8 mmol) of a sodium-bis-(trimethylsilyl)-amide solution in THF (c=2 mol/L) are chilled to −17° C. and dropwise charged with 2.00 g (11.3 mmol) 2-bromo-6-fluoropyridine. Afterwards 2.14 g (22.7 mmol) dimethyl sulfone are added and the reaction mixture is stirred at −17° C. for 1 h. The reaction is quenched by the addition of aq. sat.NaCl solution and extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877741B2uspto-grants-2014_11