Dimethyl Sulfone → HCID 86696142, compound

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

Reactant 4

HCID 6213Dimethyl Sulfone

HCID 8028Tetrahydrofuran

HCID 6394382-Bromo-6-fluoropyridine

HCID 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.