Ethanol → methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 587031Notes

Reaction equation

HRID 587031 reaction equation
C(O)C.Br[C:5]1[CH:6]=[CH:7][C:8]2[NH:14][CH2:13][CH2:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][C:9]=2[CH:19]=1.B([O-])([O-])O[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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.O>[CH2:32]([O:31][CH2:30][CH2:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:5]2[CH:6]=[CH:7][C:8]3[NH:14][CH2:13][CH2:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][C:9]=3[CH:19]=2)=[CH:27][CH:26]=1)[CH2:33][CH2:34][CH3:35]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22328963Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 867568154-Butoxyethoxyphenyl borate

Product 1

HCID 22328987methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylateYield 81.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In toluene (200 ml) and ethanol (35 ml) were suspended methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (5.0 g), 4-butoxyethoxyphenyl borate (4.6 g) and 1M potassium carbonate solution (35 ml), and the mixture was stirred for 30 minutes under argon atmosphere. Then, to the mixture was added tetrakistriphenylphosphinepalladium (1 g), and the mixture was heated at 100° C. overnight under argon atmosphere. After allowing to cool, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed a with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1) to give the solid, which was washed with hexane to give methyl 7-(4-butoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (5.7 g) as yellow crystals.

Workup

  1. temperatureto cool, to the mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed a with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1)
  7. customto give the solid, which
  8. washwas washed with hexane

Sources & evidence

ORD record
ord-54f53ed11fcd4457800dc70eeaa5d392
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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