Dimethyl Sulfone → HCID 86696142, compound

HRID 330770Notes

Reaction equation

HRID 330770 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](F)[N:13]=1.[CH3:19][S:20]([CH3:23])(=[O:22])=[O:21].[CH2:24]1COC[CH2:25]1>>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:19]2([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:25][CH2:24]2)[N:13]=1

Participants

5

Reactant 4

HCID 6213Dimethyl SulfoneHCID 8028TetrahydrofuranHCID 6394382-Bromo-6-fluoropyridineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 86696142HCID 86696142, compound

Conditions

Temperature
-17 °C

Procedure

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.

Workup

  1. customThe reaction is quenched by the addition
  2. extractionNaCl solution and extracted with EtOAc
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-84aa7a522d6045189b35bc87ee1144ae
Source dataset
uspto-grants-2014_11
Patent number
US08877741B2

Reaction notes

Loading…