Ethanol → Methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 586988Notes

Reaction equation

HRID 586988 reaction equation
[CH2:1](O)C.Br[C:5]1[CH:6]=[CH:7][C:8]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[CH2:13][CH2:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][C:9]=2[CH:27]=1.B([O-])([O-])O[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=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>[CH3:1][CH:13]1[CH2:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][C:9]2[CH:27]=[C:5]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=3)[CH:6]=[CH:7][C:8]=2[N:14]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223289287-Bromo-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 867568154-Butoxyethoxyphenyl borate

Product 1

HCID 22329269Methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

In toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) were suspended 7-bromo-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (320 mg), 4-butoxyethoxyphenyl borate (246 mg) and potassium carbonate (285 mg), and the suspension was stirred under argon atmosphere for 30 minutes. Then, to the suspension was added tetrakistriphenylphosphinepalladium (64 mg), and the mixture was heated at 100° C. for 8 hours under argon atmosphere. After allowing to cool, water was added to the mixture, 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=5:1) to give methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (207 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=5:1)

Sources & evidence

ORD record
ord-ce58d7828b984b25aa08ae3dc5802745
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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