Ammonium formate → Ethyl 3-phenyl-3-[6-(trifluoromethyl)-1H-benzimidazol-1-yl]propanoate

HRID 1676029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676029
Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:18]1([CH:11]([N:7]2[C:6]3[CH:5]=[C:4]([C:24]([F:26])([F:27])[F:25])[CH:3]=[CH:2][C:10]=3[N:9]=[CH:8]2)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 67352946Ethyl 3-[4-bromo-6-(trifluoromethyl)-1H-benzimidazol-1-yl]-3-phenyl-2-propenoate

Produkt 1

HCID 67353239Ethyl 3-phenyl-3-[6-(trifluoromethyl)-1H-benzimidazol-1-yl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-[4-bromo-6-(trifluoromethyl)-1H-benzimidazol-1-yl]-3-phenyl-2-propenoate (111 mg, 253 μmol) in ethanol (4 mL) was added palladium on carbon (23 mg, 10% w/w Pd) and ammonium formate (159 mg, 2.52 mmol). The suspension was heated to reflux for 3 hours, then cooled to room temperature, and filtered through a pad of Celite®. The filtrate was evaporated in vacuo to afford the title compound, 1H NMR: (CDCl3), 8.10 (s, 1H), 7.79 (d, J=8.79, 1H), 7.49 (s, 1H), 7.42 (d, H=8.79, 1H), 7.31-7.23 (m, 3H), 7.18-7.14 (m, 2H), 6.00 (dd, J=6.96, 6.96, 1H), 3.98 (q, J=7.32, 2H), 3.36-3.25 (m, 2H), 1.03 (t, J=7.32, 3H).

Aufarbeitung

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of Celite®
  4. customThe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-98cb5a500b0a40898a6e90fe8bc591f5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003806B2

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