Water → HCID 22329002, compound

HRID 587051Notes

Reaction equation

HRID 587051 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:9][C:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:7][C:6]=2[CH:23]=1.B([O-])([O-])O[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(O)C.O>[CH2:36]([O:35][CH2:34][CH2:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:9][C:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:7][C:6]=3[CH:23]=2)=[CH:31][CH:30]=1)[CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22328995HCID 22328995, compoundHCID 867568154-Butoxyethoxyphenyl borate

Product 1

HCID 22329002HCID 22329002, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

In toluene/ethanol/water (=10/1/1, 62.4 ml) was dissolved tert-butyl 7-bromo-1-(2-methoxyethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.8 g). To the solution were added 4-(2-butoxyethoxy)phenyl borate (1.68 g) and potassium carbonate (1.55 g), and the mixture was stirred for 30 minutes under argon atmosphere. To the mixture was added tetrakistriphenylphosphinpalladium (0.22 g), and the mixture was heated to reflux for 16 hours. After cooled to room temperature, the reaction solution was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=5/1) to give tert-butyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2-methoxyethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.4 g).

Workup

  1. additionTo the mixture was added tetrakistriphenylphosphinpalladium (0.22 g)
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 16 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=5/1)

Sources & evidence

ORD record
ord-689325dc6e6c469da9f0490873e4c184
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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