Triethylsilane → (4-Chloro-5-cyano-2-ethyl-1H-benzimidazol-1-yl)acetic acid

HRID 1188501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188501
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH3:12])[N:7]([CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:21]#[N:22].[SiH](CC)(CC)CC>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH3:12])[N:7]([CH2:13][C:14]([OH:16])=[O:15])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:21]#[N:22]

Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 690359901,1-Dimethylethyl (4-chloro-5-cyano-2-ethyl-1H-benzimidazol-1-yl)acetate

Produkt 1

HCID 67404468(4-Chloro-5-cyano-2-ethyl-1H-benzimidazol-1-yl)acetic acidAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl (4-chloro-5-cyano-2-ethyl-1H-benzimidazol-1-yl)acetate (0.032 g, 0.1 mmol) and Et3SiH (0.116 mg, 1 mmol) were combined in CH2Cl2/TFA (1:1; 6 mL) and stirred at rt for 5 h. Concentration was followed by pH adjustment to ca. 7 in H2O. Extraction with EtOAc, washing with brine, drying (Na2SO4), filtration, and concentration were followed by purification (SiO2, EtOAc/hexanes) to afford the title compound (0.017 g): MS (ESI) m/z 264 (M+1).

Aufarbeitung

  1. concentrationConcentration
  2. extractionExtraction with EtOAc
  3. washwashing with brine
  4. customdrying
  5. filtration(Na2SO4), filtration, and concentration
  6. customwere followed by purification (SiO2, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d30f7a31e33e470e8e980a44a940152f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673948B2

Notizen zur Reaktion

Wird geladen…