Ethanol → Methyl 7-(4-butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587024Notes

Reaction equation

HRID 587024 reaction equation
C(O)C.Br[C:5]1[CH:6]=[CH:7][C:8]2[N:14]([C:15]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[O:16])[CH2:13][CH2:12][C:11]([C:22]([O:24][CH3:25])=[O:23])=[CH:10][C:9]=2[CH:26]=1.B([O-])([O-])O[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:31][CH:30]=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>[CH2:39]([O:38][CH2:37][CH2:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([C:5]2[CH:6]=[CH:7][C:8]3[N:14]([C:15]([C:17]4[S:18][CH:19]=[CH:20][CH:21]=4)=[O:16])[CH2:13][CH2:12][C:11]([C:22]([O:24][CH3:25])=[O:23])=[CH:10][C:9]=3[CH:26]=2)=[CH:34][CH:33]=1)[CH2:40][CH2:41][CH3:42]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22329012Methyl 7-bromo-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylateHCID 867568154-Butoxyethoxyphenyl borate

Product 1

HCID 69750335Methyl 7-(4-butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 74.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

In toluene (10 ml), ethanol (1.0 ml) and water (1.0 ml) were suspended methyl 7-bromo-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate (210 mg), 4-butoxyethoxyphenyl borate (166 mg) and potassium carbonate (192 mg), and the mixture was stirred for 30 minutes under argon atmosphere. Then, to the suspension was added tetrakistriphenylphosphinepalladium (43 mg), and the mixture was heated at 100° C. for 5 hours 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 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=1:1) to give methyl 7-(4-butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate (201 mg) as colorless oil.

Workup

  1. temperatureto cool, to the mixture
  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=1:1)

Sources & evidence

ORD record
ord-426c8912e92042999c94eea477a2a0d0
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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