Реакция #595395

Уравнение реакции

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

Thionyl chloride

m-Anisidine

Et3N

→

desired product

Выход 48.0%

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

Выход 48.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   Температураto warm to ambient temperature over 2.5 h
3. 3
   ДругоеUpon completion, the solution was partitioned between EtOAc and H2O
4. 4
   ПромывкаThe aqueous layer was washed 3× with EtOAc
5. 5
   Промывкаthe combined organics were washed with saturated aqueous NaCl
6. 6
   Сушкаdried over Na2SO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated in vacuo
9. 9
   ДругоеThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Методика

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%).

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