Ethanol → HCID 22328984, compound

HRID 586859Notes

Reaction equation

HRID 586859 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]=[O:13])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.B([O-])([O-])O[C:21]1[CH:26]=[CH:25][C:24]([N:27]([CH2:34][CH3:35])[CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH3:33])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:34]([N:27]([C:24]1[CH:23]=[CH:22][C:21]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH:12]=[O:13])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=3[CH:18]=2)=[CH:26][CH:25]=1)[CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH3:33])[CH3:35]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22329262methyl 7-bromo-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 86756799HCID 86756799, compound

Product 1

HCID 22328984HCID 22328984, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 7-bromo-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.25 g), 4-[N-ethyl-N-(2-propoxyethyl)amino]phenyl borate (0.3 g), 1M potassium carbonate solution (2.5 ml), ethanol (2.5 ml) and toluene (25 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.04 g), and the mixture was refluxed overnight under argon atmosphere and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 7-[4-[N-ethyl-N-(2-propoxyethyl)amino]phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.31 g) as green oil.

Workup

  1. temperaturethe mixture was refluxed overnight under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4b48acb5d6c742d7b5ead0ed699c7d55
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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