N-Methyl dicyclohexylamine → 1-{(2E)-3-[4-chloro-3-(trifluoromethyl)phenyl]prop-2-en-1-yl}-1H-indole-2,3-dione

HRID 252617

Reaktionsgleichung

Reaktionsgleichung von HRID 252617
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[C:5]1=[O:14])[CH:2]=[CH2:3].Br[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=1.C1(N(C)C2CCCCC2)CCCCC1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16](/[CH:3]=[CH:2]/[CH2:1][N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:13])[C:5]2=[O:14])=[CH:17][C:18]=1[C:23]([F:24])([F:25])[F:26]

Komponenten

6

Edukt 3

HCID 24210N-Methyl dicyclohexylamineHCID 679594-Bromo-2-chloro-alpha,alpha,alpha-trifluorotolueneHCID 17135631-Allylisatin

Produkt 1

HCID 250066611-{(2E)-3-[4-chloro-3-(trifluoromethyl)phenyl]prop-2-en-1-yl}-1H-indole-2,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Six separate oven-dried sealed tubes were charged with 1-allyl-1H-indole-2,3-dione (0.100 g, 0.534 mmol), Pd(P(t-Bu)3)2 (0.0082 g, 0.016 mmol), 4-bromo-1-chloro-2-(trifluoro-methyl)benzene (0.139 g, 0.536 mmol), dry toluene (1 mL), and N-cyclohexyl-N-methyl-cyclohexanamine (0.12 mL, 0.57 mmol) under an atmosphere of N2. The tubes were heated for 16 h at 80° C. in an oil bath, and then the reactions were cooled and concentrated in vacuo. The crude material was used in the subsequent step.

Aufarbeitung

  1. customSix separate
  2. customoven-dried
  3. customsealed tubes
  4. temperaturethe reactions were cooled
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c379774113094b519c0163d5660df5b2
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868181B2

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