Sodium Cyanide → HCID 86629102, Verbindung

HRID 1097901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097901
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH:14]([CH3:28])[C:15]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=1)([OH:20])[C:16]([F:19])([F:18])[F:17])[CH2:5]OS(C)(=O)=O.[C-:29]#[N:30].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:29]#[N:30])[CH:11]=[CH:12][C:13]=1[CH:14]([CH3:28])[C:15]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=1)([OH:20])[C:16]([F:19])([F:18])[F:17]

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 86629101Methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzyl ester

Produkt 1

HCID 86629102HCID 86629102, VerbindungAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzyl ester (66 mg) was dissolved in DMF at RT under argon. Sodium cyanide (18 mg) was added and the mixture was warmed to 85° C. and allowed to stir for 1.5 hours. The mixture was diluted with ethyl acetate and washed with water and brine. The organic extracts were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give the desired compound as a colorless solid (34 mg). MS (m/e)=389.1 (MH+).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. customevaporated
  4. customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-2f2360c1d1084c3d8a8cf25d5d42992a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143280B2

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