N,N,N',N'-Tetramethylethylenediamine → 2-Fluoro-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzonitrile

HRID 500122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500122
CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:43][N:44](C)CCN(C)C.Br[C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:59]=[N:60][C:61]3[N:62]([C:64]([CH2:67][C:68]4[CH:69]=[C:70]5[C:75](=[CH:76][CH:77]=4)[N:74]=[CH:73][CH:72]=[CH:71]5)=[CH:65][N:66]=3)[N:63]=2)=[CH:54][C:53]=1[F:78]>CN(C)C=O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:78][C:53]1[CH:54]=[C:55]([C:58]2[CH:59]=[N:60][C:61]3[N:62]([C:64]([CH2:67][C:68]4[CH:69]=[C:70]5[C:75](=[CH:76][CH:77]=4)[N:74]=[CH:73][CH:72]=[CH:71]5)=[CH:65][N:66]=3)[N:63]=2)[CH:56]=[CH:57][C:52]=1[C:43]#[N:44]

Komponenten

7

Edukt 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 579711886-((2-(4-Bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl)methyl)quinoline

Produkt 1

HCID 445128962-Fluoro-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Zinc cyanide (131 mg, 1.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.038 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (78.5 mg, 0.136 mmol), and N,N,N′,N′-Tetramethylethylenediamine (0.22 mL, 1.4 mmol) were added successively to a mixture of 6-[2-(4-bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]-triazin-7-yl]methylquinoline (480 mg, 1.10 mmol) in N,N-dimethylformamide (8.7 mL) in a microwave tube. The tube was sealed and degassed three times and heated to 160° C. under microwave irradiation for 500 s. Most of the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate, water and brine, and dried over magnesium sulfate. Filtration and concentration afforded a residue which was purified on a silica gel column with methanol in dichloromethane (0-6%) to give the desired product. (90%) LCMS: (M+H)=381.0.

Aufarbeitung

  1. customThe tube was sealed
  2. customdegassed three times
  3. customMost of the solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with aqueous sodium bicarbonate, water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and concentration
  8. customafforded a residue which
  9. customwas purified on a silica gel column with methanol in dichloromethane (0-6%)

Quellen und Nachweise

ORD-Eintrag
ord-c54850f1f1674568845a95cc9927319e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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