Reacción #85720

Ecuación de reacción

(R,E)-N-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)methylene)-2-methylpropane-2-sulfinamide

methylmagnesium bromide

→

(R)—N—((R)-1-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide

Rendimiento 49.8%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was then quenched with saturated NH4Cl solution (20 mL)
2. 2
   Extracciónextracted with DCM (2×200 mL)
3. 3
   SecadoThe combined organic was dried (Na2SO4)
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was then purified via silica gel chromatography (EtOAC/heptane)

Procedimiento

To a solution of (R,E)-N-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)methylene)-2-methylpropane-2-sulfinamide (2.12 g, 6.84 mmol) in DCM (40 ml) at −40° C. was added methylmagnesium bromide (9.12 ml, 27.4 mmol). The reaction was stirred at −40° C. for 3 hours. The reaction mixture was then quenched with saturated NH4Cl solution (20 mL). The aqueous layer was adjusted to pH=8 with HCl (1M) and extracted with DCM (2×200 mL). The combined organic was dried (Na2SO4) and concentrated. The residue was then purified via silica gel chromatography (EtOAC/heptane) to give (R)—N—((R)-1-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide (1.11 g). LCMS (B) m/z 326.3 (M+H)+

Fuente