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Potassium Carbonate → Methyl 7-(4-morpholinophenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 1277253
Notes
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Reaction equation

HRID 1277253 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[O:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][C:19]([C:2]3[CH:3]=[CH:4][C:5]4[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=4[CH:16]=3)=[CH:20][CH:21]=2)[CH2:26][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18472606HCID 18472606, compoundHCID 867561794-Morpholinophenyl borate

Product 1

HCID 18472523Methyl 7-(4-morpholinophenyl)-2,3-dihydro-1-benzothiepine-4-carboxylateYield 74.4%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

Under argon atmosphere, a mixture of methyl 7-bromo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.70 g), 4-morpholinophenyl borate (581.3 mg) and potassium carbonate (0.65 g) in toluene/ethanol/water (20/2/2 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphine palladium (0.14 g), and the mixture was refluxed for 20 hours and then cooled. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/dichloromethane=1:4) to give yellow crystals of methyl 7-(4-morpholinophenyl)-2,3-dihydro-1-benzo-thiepine-4-carboxylate (664.4 mg).

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationUnder reduced pressure, the mixture was concentrated
  7. customthe residue was purified with column chromatography (ethyl acetate/dichloromethane=1:4)

Sources & evidence

ORD record
ord-c0b52041c8664e8a9a9a4a756d82bb46
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06166006

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes