Methyl bromoacetate → HCID 13067116, compound

HRID 1388610Notes

Reaction equation

HRID 1388610 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]3[C:7](=[CH:18][NH:19][CH:20]=3)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32]>CN(C)C=O.O>[CH3:34][O:33][C:31](=[O:32])[CH2:30][N:19]1[CH:20]=[C:6]2[C:7]([CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:22]=[CH:21][C:5]=32)=[CH:18]1

Participants

6

Reactant 3

HCID 60984Methyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 136045442HCID 136045442, compound

Product 1

HCID 13067116HCID 13067116, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In one portion 2.0 g (6.4 mmol) of 8-chloro-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 0.9 g (8 mmol) of potassium t-butoxide in 30 ml of dimethylformamide which was cooled to 0°. After stirring for 15 min, 0.7 ml (7.5 mmol) of methyl bromoacetate was added. The mixture was stirred for 5 min, diluted with water and extracted with ether. The ether solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. Purification of the residue by column chromatography gave a pale yellow oil.

Workup

  1. temperaturewas cooled to 0°
  2. stirringThe mixture was stirred for 5 min
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure to dryness
  7. customPurification of the residue by column chromatography
  8. customgave a pale yellow oil

Sources & evidence

ORD record
ord-336f8efd014846e3afbc18e31b082a18
Source dataset
uspto-grants-1984_02
Patent number
US04431823

Reaction notes

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