Water → ethyl 5,6,7,8-tetrahydro-11-bromomethyl-8-oxo-4H-azocino [3.2.1-hi]indole-2-carboxylate

HRID 650086노트

반응식

HRID 650086 반응식
CC1C=CC=C2C=1C=C(C(OCC)=O)N2.[CH3:16][C:17]1[CH:25]=[CH:24][C:23]2[C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH2:30][N:21]3[C:22]=2[C:18]=1[CH:19]=[C:20]3[C:32]([O:34][CH2:35][CH3:36])=[O:33].[Br:37]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:37][CH2:16][C:17]1[CH:25]=[CH:24][C:23]2[C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH2:30][N:21]3[C:22]=2[C:18]=1[CH:19]=[C:20]3[C:32]([O:34][CH2:35][CH3:36])=[O:33]

참가 물질

7

반응물 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 12529972Ethyl 4-methyl-1H-indole-2-carboxylateHCID 70237721Ethyl 5,6,7,8-tetrahydro-11-methyl-8-oxo-4H-azocino [3.2.1-hi]indole-2-carboxylate2회

생성물 1

HCID 70238124ethyl 5,6,7,8-tetrahydro-11-bromomethyl-8-oxo-4H-azocino [3.2.1-hi]indole-2-carboxylate

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

In accordance with the process described in Example 22(a)-(c) except for using ethyl 4-methyl-1H-indole-2-carboxylate as a starting material, ethyl 5,6,7,8-tetrahydro-11-methyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate (m.p. 98° C., recrystallized from isopropyl alcohol) was synthesized. Ethyl 5,6,7,8-tetrahydro-11-methyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate (2.50 g, 8.76 mmol) was then dissolved in carbon tetrachloride (80 ml) and N-bromosuccinimide (1.72 g, 9.64 mmol) and 2,2′-azobisisobutyronitrile (43 mg) were added therein under refluxing condition to heat at reflux for 2 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off and the obtained residue was purified with silica gel column chromatography (eluated with ethyl acetate/n-hexane=1/10) to give ethyl 5,6,7,8-tetrahydro-11-bromomethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate (3.12 g).

후처리

  1. customwas synthesized
  2. temperatureunder refluxing condition
  3. temperatureto heat
  4. temperatureat reflux for 2 hours
  5. extractionextracted with chloroform
  6. washThe extract was washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe obtained residue was purified with silica gel column chromatography (eluated with ethyl acetate/n-hexane=1/10)

출처 및 근거

ORD 기록
ord-0c80873a781b4948ab86b839d659bdcf
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271251B1

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