2,3,6-Trifluoroaniline → ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate

HRID 2368485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368485
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH:18]=O)=[CH:4][CH:3]=1.[F:20][C:21]1[C:27]([F:28])=[CH:26][CH:25]=[C:24]([F:29])[C:22]=1[NH2:23].[B][B][B][B][B][B][B][B][B][B]>C(O)(=O)C.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][NH:23][C:22]2[C:24]([F:29])=[CH:25][CH:26]=[C:27]([F:28])[C:21]=2[F:20])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 5222832,3,6-TrifluoroanilineHCID 86677543ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylateHCID 178419135HCID 178419135, Verbindung

Produkt 1

HCID 71117752ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate (16) (150 mg, 0.57 mmol), 2,3,6-trifluoroaniline (60.4 μL, 0.57 mmol), decaborane (14 mg, 0.11), acetic acid (2 drops), and methanol (6 mL) was stirred at room temperature overnight. The reaction was concentrated and the residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes) to yield ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate (23).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dfbce6092f9649448ca2ce99c4f81893
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703776B2

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