1-Fluoro-3-nitrobenzene → Ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate

HRID 1067831노트

반응식

HRID 1067831 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

참가 물질

5

반응물 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 21194451HCID 21194451, 화합물

생성물 1

HCID 21194305Ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate수율 24.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

After 0.50 g (1.97 mmol) of ethyl 4-chloro-7-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.16 g (3.94 mmol) of 60% sodium hydride and 10 ml of dimethylformamide, the suspension was stirred at room temperature for 30 minutes. Then 0.28 g (1.97 mmol) of 1-fluoro-3-nitrobenzene was added to the solution at room temperature followed by stirring for 3 hours at 150° C. After cooling, the reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 0.18 g (24.3%) of ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate.

후처리

  1. stirringby stirring for 3 hours at 150° C
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto ice water
  4. extractionThe resulting mixture was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was isolated
  9. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2aab6ffc57ee4292a6b2b2de09700c4a
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248772B1

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