Reacción #417952

ord-84aa7a522d6045189b35bc87ee1144ae

Ecuación de reacción

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

Condiciones de reacción

Temperatura
-17°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe reaction is quenched by the addition
  2. 2
    ExtracciónNaCl solution and extracted with EtOAc
  3. 3
    SecadoThe organic layer is dried over MgSO4
  4. 4
    Filtraciónfiltered
  5. 5
    Otrothe solvent is removed in vacuo

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08877741B2uspto-grants-2014_11