Triethylamine → 1-[3-(3,4-dichlorophenyl)prop-2-yn-1-yl]-1H-indole-2,3-dione

HRID 252619

Reaktionsgleichung

Reaktionsgleichung von HRID 252619
[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])[C:2]#[CH:3].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:17]=1[Cl:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.[Cu]I.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:15][C:16]1[CH:21]=[C:20]([C:3]#[C: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:19]=[CH:18][C:17]=1[Cl:23]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 88591Benzene, 1,2-dichloro-4-iodo-HCID 19090021-(Prop-2-yn-1-yl)-1H-indole-2,3-dione

Produkt 1

HCID 247514551-[3-(3,4-dichlorophenyl)prop-2-yn-1-yl]-1H-indole-2,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-prop-2-yn-1-yl-1H-indole-2,3-dione (190 mg, 1.03 mmol), 1,2-dichloro-4-iodobenzene (420 mg, 1.54 mmol), copper(I) iodide (11.0 mg, 0.06 mmol) and triphenylphosphine (40.0 mg, 0.15 mmol) in degassed DMF (24 mL) was added triethyl-amine (307 μL, 2.15 mmol). The reaction was stirred for 5 minutes and Pd(OAc)2 (13.0 mg, 0.06 mmol) was then added. The reaction was stirred at room temperature for 2 days, concentrated in vacuo, dissolved in EtOAc and washed with saturated NaHCO3(aq) (1×). The layers were separated and the aqueous layer was extracted with additional EtOAc (2×).

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 2 days
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in EtOAc
  4. washwashed with saturated NaHCO3(aq) (1×)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with additional EtOAc (2×)

Quellen und Nachweise

ORD-Eintrag
ord-5c6cdf3ed42446a68ecd894a57df221c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868181B2

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