反応 #595395

反応方程式

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

Thionyl chloride

m-Anisidine

Et3N

→

desired product

収率 48.0%

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

収率 48.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   温度to warm to ambient temperature over 2.5 h
3. 3
   その他Upon completion, the solution was partitioned between EtOAc and H2O
4. 4
   洗浄The aqueous layer was washed 3× with EtOAc
5. 5
   洗浄the combined organics were washed with saturated aqueous NaCl
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

実験手順

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%).

出典