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Cesium fluoride → 1-{[2,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione

HRID 1513336
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HRID 1513336 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14](Br)[C:13]1=[O:20].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[F-].[Cs+]>[Cl-].C([N+](CC)(CC1C=CC=CC=1)CC)C.C1(C)C=CC=CC=1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:13](=[O:20])[C:14]([C:26]2[CH:27]=[CH:28][C:23]([C:22]([F:33])([F:32])[F:21])=[CH:24][CH:25]=2)=[C:15]([CH3:18])[C:16]1=[O:17]
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참가 물질

8

반응물 3

HCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 12013927{[2,4-bis(methyloxy)phenyl]methyl}-3-bromo-4-methyl-1H-pyrrole-2,5-dione

생성물 1

HCID 594961041-{[2,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione수율 115.7%

시약·촉매·용매 4

HCID 66133
Benzyl triethylammonium chloride
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

{[2,4-bis(methyloxy)phenyl]methyl}-3-bromo-4-methyl-1H-pyrrole-2,5-dione (P9, 3.3, 9.7 mmol), [4-(trifluoromethyl)phenyl]boronic acid (3.68 g, 19.40 mmol), bis(triphenylphosphine)palladium(ii) chloride (0.601 g, 0.91 mmol) and cesium fluoride (3.98 g, 26.2 mmol) and N,N-diethyl-N-(phenylmethyl)ethanaminium chloride (0.22 g, 0.970 mmol) were dissolved in Toluene (60 mL)/Water (60.0 mL) and the reaction mixture was stirred at 90° C. overnight. Toluene was evaporated under reduced pressure and a saturated solution of NH4Cl was added. The aqueous phase was extracted with DCM, solvent was eliminated under reduced pressure and crude product by flash chromatography (Biotage SiO2, eluent: Cy/AcOEt 98:2; fraction volume: 45 mL) affording 1-{[2,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione (P10, 4.55 g, 11.22 mmol)

후처리

  1. customToluene was evaporated under reduced pressure
  2. additiona saturated solution of NH4Cl was added
  3. extractionThe aqueous phase was extracted with DCM, solvent

출처 및 근거

ORD 기록
ord-ab6cb544f80e496a894af18528d2791b
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217168B2

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