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Triphenylphosphine → 3-fluoro-N-{2-[2-(trimethylsilyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]ethyl}benzamide

HRID 1847212
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1847212
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[F:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([NH:15][CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[Na+].[Cl-].[Li+]>CN(C)C=O.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([NH:15][CH2:16][CH2:17][C:18]1[C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH:8][C:19]=1[Si:20]([CH3:22])([CH3:21])[CH3:23])=[O:14]
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Komponenten

10

Edukt 5

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 517045Sodium AcetateHCID 15165104-Amino-3-iodopyridineHCID 672549453-fluoro-N-[4-(trimethylsilyl)-3-butynyl]benzamide

Produkt 1

HCID 672549103-fluoro-N-{2-[2-(trimethylsilyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]ethyl}benzamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 3-iodo-4-pyridineamine (594 mg), 3-fluoro-N-[4-(trimethylsilyl)-3-butynyl]benzamide (710 mg), palladium acetate (61 mg), triphenylphosphine (142 mg), sodium acetate (443 mg) and lithium chloride (115 mg) in N,N-dimethylformamide (6 mL) and acetonitrile (3 mL) was irradiated with microwave (100 W) for 30 minutes, poured into water and then extracted with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (parallel separation purification system) to obtain the titled compound having the following physical properties (404.8 mg).

Aufarbeitung

  1. customwas irradiated with microwave (100 W) for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (parallel separation purification system)

Quellen und Nachweise

ORD-Eintrag
ord-17b21918380847eb8e592f92346e8a1f
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952158B2

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