Potassium Carbonate → HCID 21995659, compound

HRID 1978580Notes

Reaction equation

HRID 1978580 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]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-:31].[K+].[K+].C1(C)C=CC=CC=1.C(O)C.[OH2:46]>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>[CH:25]([C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[S:11](=[O:31])(=[O:46])[CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=3[CH:16]=2)=[CH:20][CH:21]=1)([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18472606HCID 18472606, compoundHCID 86587398Ethanol toluene waterHCID 86756176HCID 86756176, compound

Product 1

HCID 21995659HCID 21995659, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Under argon atmosphere, a mixture of methyl 7-bromo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.80 g), 4-isopropylphenyl borate (0.44 g) and potassium carbonate (0.67 g) in toluene/ethanol/water (30/3/3 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphinepalladium (0.14 g), and the mixture was refluxed for 20 hours, cooled, extracted with ethyl acetate, washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (ethyl acetate/hexane=1:2) to give pale yellow crystals of methyl 7-(4-isopropylphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (774.7 mg).

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with column chromatography (ethyl acetate/hexane=1:2)

Sources & evidence

ORD record
ord-8bfd0adb2e644eb6bc8086f0f324dee3
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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