Ethanol → Methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 586980Notes

Reaction equation

HRID 586980 reaction equation
C(O)C.[CH2:4]([N:7]1[C:13]2[CH:14]=[CH:15][C:16](Br)=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]([O:21][CH3:22])=[O:20])[CH2:9][CH2:8]1)[CH:5]=[CH2:6].B([O-])([O-])O[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][CH3:37])=[CH:27][CH:26]=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>[CH2:4]([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][CH3:37])=[CH:27][CH:26]=3)=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]([O:21][CH3:22])=[O:20])[CH2:9][CH2:8]1)[CH:5]=[CH2:6]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 11324721Methyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylateHCID 867568144-(2-Propoxyethoxy)phenyl borate

Product 1

HCID 69747248Methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In toluene (20 ml), ethanol (2 ml) and water (2 ml) were suspended methyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (274 mg), 4-propoxyethoxyphenyl borate (248 mg) and potassium carbonate (307 mg), and the suspension was stirred under argon atmosphere for 30 minutes, Then, tetrakistriphenylphosphinepalladium (69 mg) was added thereto, and the mixture was heated under argon atmosphere at 100° C. for 8 hours. After allowing to cool, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed 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 methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (269 mg) as yellow oil.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed 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)

Sources & evidence

ORD record
ord-679d486d1b6846e6bcaafa77d1a0c2bb
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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