Ethyl bromoacetate → 8-Chloro-6-phenyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid ethyl ester

HRID 2296272Notes

Reaction equation

HRID 2296272 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:27]=[CH:26][C:11]2[C:12]3[C:13](=[CH:23][NH:24][CH:25]=3)[CH2:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[CH:9]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C)C=O.O>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:24]1[CH:25]=[C:12]2[C:13]([CH2:14][N:15]=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:10]3[CH:9]=[C:8]([Cl:7])[CH:27]=[CH:26][C:11]=32)=[CH:23]1)[CH3:34]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 1360876848-Chloro-6-phenyl-2H,4H-pyrrolo[3,4-d][2]benzazepine

Product 1

HCID 130671008-Chloro-6-phenyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.4 g (12.4 mmole) of potassium t-butoxide in 30 ml of dry dimethylformamide was added 2.4 g (8.2 mmole) of 8-chloro-6-phenyl-2H,4H-pyrrolo[3,4-d][2]benzazepine. The mixture was cooled to 0°, and stirred for 10 min. To the mixture was added 1.3 mol (11.7 mmole) of ethyl bromoacetate. The mixture was stirred at 0° for 45 min, diluted with water, and extracted with ether. The ether solution was washed with water, dried with sodium sulfate, and concentrated at reduced pressure to give a yellow oil. Purification by column chromatography (70 g SiO2, 9:1 methylene chloride/ether) gave as the first major component a yellow oil.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. stirringThe mixture was stirred at 0° for 45 min
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto give a yellow oil
  8. customPurification by column chromatography (70 g SiO2, 9:1 methylene chloride/ether)
  9. customgave as the first major component a yellow oil

Sources & evidence

ORD record
ord-28ffc8eff3544997b6f160676a0bec6c
Source dataset
uspto-grants-1984_01
Patent number
US04428878

Reaction notes

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