5-Bromo-4-chloro-2-ethyl-1-(2,2,2-trifluoroethyl)-1H-benzimidazole → 4-Chloro-2-ethyl-1-(2,2,2-trifluoroethyl)-1H-benzimidazole-5-carbonitrile

HRID 1188494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188494
Br[C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH2:11][C:12]([F:15])([F:14])[F:13])[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[C:3]=1[Cl:18].[C:19]([Cu])#[N:20]>CN1C(=O)CCC1>[Cl:18][C:3]1[C:4]2[N:8]=[C:7]([CH2:9][CH3:10])[N:6]([CH2:11][C:12]([F:15])([F:14])[F:13])[C:5]=2[CH:16]=[CH:17][C:2]=1[C:19]#[N:20]

Komponenten

4

Edukt 2

HCID 578001385-Bromo-4-chloro-2-ethyl-1-(2,2,2-trifluoroethyl)-1H-benzimidazoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 674075814-Chloro-2-ethyl-1-(2,2,2-trifluoroethyl)-1H-benzimidazole-5-carbonitrileAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

5-Bromo-4-chloro-2-ethyl-1-(2,2,2-trifluoroethyl)-1H-benzimidazole (0.036 g, 0.106 mmol) and CuCN (0.020 g, 0.222 mmol) were combined in NMP (3 mL) and heated to 220° C. for 20 min in a microwave. The cooled mixture was partitioned between Et2O and water, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.015 g): 1NMR (400 MHz, CDCl3) δ 7.56 (d, J=8.4 Hz, 1H), 7.34 (d, J=8.4 Hz, 1H), 4.68 (q, J=8.2 Hz, 2H), 2.96 (q, J=7.4 Hz, 2H), 1.45 (t, J=7.4 Hz, 3H); MS (ESI) m/z 288 (M+1).

Aufarbeitung

  1. customThe cooled mixture was partitioned between Et2O and water
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification (SiO2, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1a9c5300d8754055997997e48b37a60c
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673948B2

Notizen zur Reaktion

Wird geladen…