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

HRID 566079Notes

Reaction equation

HRID 566079 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

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-benzothiepine-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-e2bf77c8705746a4b32ade1db58dd99c
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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