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

HRID 1600647ノート

反応式

HRID 1600647 の反応式
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]

参加物

7

反応物 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-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1cf4cae8a1a848df86c037189cb75f3c
出典データセット
uspto-grants-1999_11
特許番号
US05977100

反応ノート

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