Triethylamine → 3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1829048

Reaktionsgleichung

Reaktionsgleichung von HRID 1829048
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2.[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[CH:25].C(N(CC)CC)C>CN(C=O)C.CO.[Cu]I.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>[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[C:25][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 81643N,N-DimethylpropargylamineHCID 696592423-(5-Bromo-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 696591513-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-oneAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a mixture of 3-(5-bromo-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (467 mg, 1.42 mmol), 1-dimethylamino-2-propyne (473 mg, 5.69 mmol), copper(I) iodide (48 mg, 0.25 mmol), triethylamine (287 mg, 2.84 mmol) in DMF (5 ml), was added tetrakis(triphenylphosphine)palladium (100 mg, 0.086 mmol). The mixture was heated at 65° C. under argon for 16 hours, and then cooled to room temperature. The mixture was diluted with MeOH (100 ml). The insoluble material was removed by filtration, and the filtrate solution was concentrated and then diluted with EtOAc (200 ml). The resulting mixture was washed with brine (3×100 ml), dried over anhydrous Na2SO4, and concentrated to give a dark-brown residue. Purification of the residue by silica gel column chromatography, eluted with a gradient of MeOH in CHCl3, afforded 3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a brown solid (320 mg, 68%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate solution was concentrated
  4. additiondiluted with EtOAc (200 ml)
  5. washThe resulting mixture was washed with brine (3×100 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto give a dark-brown residue
  9. customPurification of the residue by silica gel column chromatography
  10. washeluted with a gradient of MeOH in CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-be0939c8a573433199b87c0311c98046
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060844B2

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