تفاعل #595395

معادلة التفاعل

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

Thionyl chloride

m-Anisidine

Et3N

→

desired product

المردود 48.0%

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

المردود 48.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   درجة الحرارةto warm to ambient temperature over 2.5 h
3. 3
   أخرىUpon completion, the solution was partitioned between EtOAc and H2O
4. 4
   غسيلThe aqueous layer was washed 3× with EtOAc
5. 5
   غسيلthe combined organics were washed with saturated aqueous NaCl
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

الإجراء التجريبي

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%).

المصدر