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5-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile → 5-(5-formyl-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

HRID 506193
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 506193
I[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:9]=1[NH:10][C:11]1[C:12]([CH3:20])=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:7]#[N:8].C([Sn](CCCC)(CCCC)[C:26]1[O:27][C:28]2[CH:34]=[CH:33][C:32]([CH:35]=[O:36])=[CH:31][C:29]=2[CH:30]=1)CCC>CN(C=O)C.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>[CH:35]([C:32]1[CH:33]=[CH:34][C:28]2[O:27][C:26]([C:2]3[CH:3]=[N:4][CH:5]=[C:6]([C:9]=3[NH:10][C:11]3[C:12]([CH3:20])=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH:15]=[CH:14]4)[C:7]#[N:8])=[CH:30][C:29]=2[CH:31]=1)=[O:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 684438315-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrileHCID 866168342-(Tributylstannyl)-1-benzofuran-5-carbaldehyde

Produkt 1

HCID 866168355-(5-formyl-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrileAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile (2.5 g, 6.7 mmol), 2-(tributylstannyl)-1-benzofuran-5-carbaldehyde (4.35 g, 10 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.38 g, 0.34 mmol) in DMF (25 mL) was heated at 120° C. for 1 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water, resulting in a suspension. The insoluble material was removed by filtration and the residue was washed thoroughly with ethyl acetate. The organic layer (from filtrate) was washed with water twice and brine, dried over sodium sulfate, and concentrated and the residue was purified by column chromatography (ethyl acetate/hexane, 1:1) to give 2.0 g (76%) of 5-(5-formyl-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile as a yellow solid. HPLC retention time: 10.7 min.(h); MS: 393.2 (M+H); melting point: 235-237° C.; and HRMS: 393.13484.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. customresulting in a suspension
  4. customThe insoluble material was removed by filtration
  5. washthe residue was washed thoroughly with ethyl acetate
  6. washThe organic layer (from filtrate) was washed with water twice
  7. dry with materialbrine, dried over sodium sulfate
  8. concentrationconcentrated
  9. customthe residue was purified by column chromatography (ethyl acetate/hexane, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3835316e2c3741ae8981c9e2bfb8ef04
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781591B2

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