Reacción #595395

Ecuación de reacción

3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoic acid

Thionyl chloride

m-Anisidine

Et3N

→

desired product

Rendimiento 48.0%

3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxy-N-(3-methoxyphenyl)-propanamide

Rendimiento 48.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturato warm to ambient temperature over 2.5 h
3. 3
   OtroUpon completion, the solution was partitioned between EtOAc and H2O
4. 4
   LavadoThe aqueous layer was washed 3× with EtOAc
5. 5
   Lavadothe combined organics were washed with saturated aqueous NaCl
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Procedimiento

3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoic acid (0.025 g, 0.061 mmol) was suspended in anhydrous CH2Cl2 and cooled to 0° C. Thionyl chloride (0.005 mL, 0.073 mmol) was added dropwise and the reaction was stirred at 0° C. for 1 h. m-Anisidine (0.008 mL, 0.073 mmol) and Et3N (0.010 mL, 0.073 mmol) were added and the reaction was allowed to warm to ambient temperature over 2.5 h. Upon completion, the solution was partitioned between EtOAc and H2O. The aqueous layer was washed 3× with EtOAc, and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane) to afford the desired product (15 mg, 48%).

Fuente