Ethanol → Methyl 7-(4-propoxyphenyl)-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587011Notes

Reaction equation

HRID 587011 reaction equation
C(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]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:13][CH2:12][C:11]([C:24]([O:26][CH3:27])=[O:25])=[CH:10][C:9]=2[CH:28]=1.B([O-])([O-])O[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH3:40])=[CH:33][CH:32]=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>[CH2:38]([O:37][C:34]1[CH:35]=[CH:36][C:31]([C:5]2[CH:6]=[CH:7][C:8]3[N:14]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH3:23])[CH2:13][CH2:12][C:11]([C:24]([O:26][CH3:27])=[O:25])=[CH:10][C:9]=3[CH:28]=2)=[CH:32][CH:33]=1)[CH2:39][CH3:40]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22329284Methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylateHCID 867567774-Propoxyphenyl borate

Product 1

HCID 22329240Methyl 7-(4-propoxyphenyl)-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 81.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

In toluene (25 ml), ethanol (2.5 ml) and water (2.5 ml) were suspended methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate (712 mg), 4-propoxyphenyl borate (416 mg) and potassium carbonate (636 mg), and the suspension was stirred under argon atmosphere for 30 minutes. Then, to the suspension was added tetrakistriphenylphosphinepalladium (143 mg) and the mixture was heated under argon atmosphere at 100° C. for 5 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=3:1) to give methyl 7-(4-propoxyphenyl)-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate (663 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=3:1)

Sources & evidence

ORD record
ord-af8d9103562c4d53a3fe5ab3646c1356
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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