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Hexane → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2,4-difluorophenyl)oxindole

HRID 1369109
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1369109
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[Li]CCCC.CCCCCC.[CH2:21]([N:23]([CH2:42][CH3:43])[CH2:24][CH2:25][N:26]1[C:36]2[C:31](=[C:32]([C:38]([F:41])([F:40])[F:39])[CH:33]=[C:34]([I:37])[CH:35]=2)[C:29](=[O:30])[C:27]1=[O:28])[CH3:22]>C1COCC1>[CH2:42]([N:23]([CH2:21][CH3:22])[CH2:24][CH2:25][N:26]1[C:36]2[C:31](=[C:32]([C:38]([F:39])([F:41])[F:40])[CH:33]=[C:34]([I:37])[CH:35]=2)[C:29]([OH:30])([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[F:9])[C:27]1=[O:28])[CH3:43]
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Komponenten

6

Edukt 4

HCID 8058HexaneHCID 676741-Bromo-2,4-difluorobenzeneHCID 110265521-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodoisatinHCID 178418339Butyllithium

Produkt 1

HCID 185185481-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2,4-difluorophenyl)oxindoleAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-bromo-2,4-difluorobenzene (0.13 mL, 1.15 mmol) in THF (7.5 mL) was added dropwise 1.47 N BuLi in hexane (0.77 mL, 1.13 mmol) at −78° C. and the mixture was stirred for 15 min. To the resulting solution was added dropwise a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin (500 mg, 1.14 mmol) in THF (6 mL) over 15 min at −78° C. The mixture was stirred for 40 min at the same temperature and the reaction was quenched with aqueous NaHCO3. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol to give the title compound (576 mg, 91%).

Aufarbeitung

  1. stirringThe mixture was stirred for 40 min at the same temperature
  2. customthe reaction was quenched with aqueous NaHCO3
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol

Quellen und Nachweise

ORD-Eintrag
ord-4fcf88a7d5514c4ba35a2a282486b947
Quelldatensatz
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06576656B1

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