Reacción #612705

Ecuación de reacción

tri-2-furylphosphine

2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(trimethylstannyl)-phenyl)-oxazolidin-3-yl)ethanone

N-((5-bromopyridin-2-yl)methyl)ethanesulfonamide

→

title compound

Rendimiento 43.1%

N-((5-(4-((4S,5R)-3-(2,2-dichloroacetyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)phenyl)pyridin-2-yl)methyl)-ethanesulfonamide

Rendimiento 43.1%

Disolventes

N-Methyl-2-pyrrolidone

ethylacetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropurged with nitrogen gas
2. 2
   TemperaturaThe reaction mixture is cooled
3. 3
   Lavadowashed with water
4. 4
   SecadoThe organic phase is dried (Na2SO4)
5. 5
   Concentraciónconcentrated under vacuum
6. 6
   OtroThe crude material is chromatographed (24 g Redi-Sep column)
7. 7
   Lavadoeluting from 100% hexanes to 90:10 ethylacetate

Procedimiento

2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(trimethylstannyl)-phenyl)-oxazolidin-3-yl)ethanone (281 mg, 0.66 mmol) and N-((5-bromopyridin-2-yl)methyl)ethanesulfonamide (155 mg, 0.56 mmol) are dissolved in N-Methyl-2-pyrrolidone (40 mL) and purged with nitrogen gas. Pd2(dba)3 (51 mg, 0.055 mmol) and tri-2-furylphosphine (27 mg, 0.11 mmol) are added; the resulting mixture is heated to 80° C. for 18 hours. The reaction mixture is cooled, diluted with ethylacetate, and washed with water. The organic phase is dried (Na2SO4) and concentrated under vacuum. The crude material is chromatographed (24 g Redi-Sep column) eluting from 100% hexanes to 90:10 ethylacetate:hexanes to afford the title compound (125 mg): m/z (Cl) M+H 518.

Fuente