Chloride → methyl 7-bromo-1-(2-oxopropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 587089Notes

Reaction equation

HRID 587089 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][CH:14]=[CH2:15])[CH2:11][CH2:10][C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:7]=2[CH:20]=1.CN(C=[O:25])C.O>[Cl-].[Na+].O.[Pd](Cl)Cl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14](=[O:25])[CH3:15])[CH2:11][CH2:10][C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:7]=2[CH:20]=1

Participants

6

Reactant 3

HCID 312ChlorideHCID 11324721Methyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylateHCID 21962138N,N-Dimethylformamide--water (1/1)2×

Product 1

HCID 22329093methyl 7-bromo-1-(2-oxopropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of palladium chloride (96 mg) and curious chloride (218 mg) in DMF-water (7-1 ml) was stirred at 60° C. for 18 hours under oxygen atmosphere. To the reaction system was added a solution of methyl 7-bromo-1-(2-propenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (500 mg) in DMF-water (7-1 ml) was added, and the mixture was stirred at 60° C. for 7 hours. To the reaction system was added saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate:hexane=1:4→1:2) to give methyl 7-bromo-1-(2-oxopropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (311 mg) as yellow crystals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 60° C. for 7 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was separated
  8. custompurified with column chromatography (ethyl acetate:hexane=1:4→1:2)

Sources & evidence

ORD record
ord-d62baa39a8034789a8c9b053dec03673
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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