Potassium Carbonate → HCID 21995772, 화합물

HRID 1978760노트

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HRID 1978760 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:31])[CH:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:19][CH:18]=3)=[O:15])=[CH:7][C:6]=2[CH:32]=1.C1(C)C=CC=CC=1.C(O)C.O.B([O-])([O-])O[C:46]1[CH:47]=[CH:48][C:49]2[O:53][C:52]([CH2:54][O:55][CH2:56][CH2:57][CH3:58])=[CH:51][C:50]=2[CH:59]=1.C(=O)([O-])[O-].[K+].[K+]>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>[CH3:31][N:24]([CH2:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14]([C:8]2[CH2:9][CH2:10][S:11](=[O:13])(=[O:12])[C:5]3[CH:4]=[CH:3][C:2]([C:46]4[CH:47]=[CH:48][C:49]5[O:53][C:52]([CH2:54][O:55][CH2:56][CH2:57][CH3:58])=[CH:51][C:50]=5[CH:59]=4)=[CH:32][C:6]=3[CH:7]=2)=[O:15])=[CH:18][CH:19]=1)[CH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 219957067-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamideHCID 86587398Ethanol toluene waterHCID 86756844HCID 86756844, 화합물

생성물 1

HCID 21995772HCID 21995772, 화합물수율 37.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

To 7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (0.41 g) was added toluene/ethanol/water (10/1/1,19.2 ml) and then were added 2-(propoxymethyl)-1-benzofuran-5-yl borate (0.22 g) and potassium carbonate (0.24 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (45 mg), and the mixture was refluxed for 14 hours, cooled to room temperature and poured into water. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed, and the residue was purified with silica gel column chromatography (ethyl acetate/ethanol=4/1) and recrystallized from ethanol to give N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-[2-(propoxymethyl)-1-benzofuran-5-yl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 136) (184 mg).

후처리

  1. temperaturethe mixture was refluxed for 14 hours
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was removed
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate/ethanol=4/1)
  8. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-6ae2819e62b84483bd181589f1f566b4
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235771B1

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