Trimethylsilyl cyanide → (7-Methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 2079162

Reaktionsgleichung

Reaktionsgleichung von HRID 2079162
C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].[CH3:26][C:27]1[O:31][N:30]=[C:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[N:28]=1.[CH3:39][O:40][C:41]1[C:49]2[O:48][CH2:47][CH2:46][C:45]=2[CH:44]=[C:43]([CH:50]=O)[CH:42]=1.FC(F)(F)C(O)=O.[C:59](C1C=CC(NC(C2C=C(OC)C(OC)=CC=2F)C2NC(=O)N(C3C=CC=CC=3C(O)=O)N=2)=CC=1)(=N)[NH2:60].C[Si](C#N)(C)C>C1COCC1>[CH3:39][O:40][C:41]1[C:49]2[O:48][CH2:47][CH2:46][C:45]=2[CH:44]=[C:43]([CH:50]([NH:38][C:35]2[CH:36]=[CH:37][C:32]([C:29]3[N:28]=[C:27]([CH3:26])[O:31][N:30]=3)=[CH:33][CH:34]=2)[C:59]#[N:60])[CH:42]=1

Komponenten

7

Edukt 5

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 223438017-Methoxy-2,3-dihydrobenzofuran-5-carbaldehydeHCID 1363370832-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid Trifluoroacetate

Produkt 1

HCID 67096962(7-Methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 426 mg of Yb(OTf)3 in 30 ml of THF there were added 1.2 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1.22 g of 7-methoxy-2,3-dihydrobenzofuran-5-carbaldehyde [CAS No. 363185-46-0], 1g of MS3A and 1.9 ml of trimethylsilyl cyanide under a nitrogen atmosphere, and the mixture was stirred at room temperature. The reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give a crude product of (7-methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with 100 ml of ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbb87a5c4d7d450a8e6e9fc0bd136f52
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928228B2

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