Dimethylformamide → 2-butyl-4-[4-(4-ethyl-hexyloxy)-phenyl]-1-[4-(4-methoxy-naphthalen-1-yl-oxy)-phenyl]-1H-imidazole

HRID 901707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901707
C(N(CC)[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH3:15])=[CH:10][CH:9]=1)C.[CH2:19]1[CH2:24][NH:23][C:21](=O)[CH2:20]1.Br[Br-]Br.[CH3:28][O:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([O:40][C:41]2[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=2)=[CH:32][CH:31]=1.[CH3:48]N(C=O)C.Br[CH2:54][C:55]([C:57]1C=CC(OCCCN(CC)CC)=[CH:59][CH:58]=1)=O>CO.O.CCOC(C)=O>[CH2:19]([C:24]1[N:45]([C:44]2[CH:43]=[CH:42][C:41]([O:40][C:33]3[C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:30]([O:29][CH3:28])=[CH:31][CH:32]=3)=[CH:47][CH:46]=2)[CH:15]=[C:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][CH2:4][CH:57]([CH2:58][CH3:59])[CH2:55][CH3:54])=[CH:13][CH:12]=2)[N:23]=1)[CH2:20][CH2:21][CH3:48]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 118583611-(4-[3-(Diethylamino)propoxy]phenyl)ethanoneHCID 669774504-(4-Methoxy-naphthalen-1-yloxy)anilineHCID 865919692-Bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

Produkt 1

HCID 669775342-butyl-4-[4-(4-ethyl-hexyloxy)-phenyl]-1-[4-(4-methoxy-naphthalen-1-yl-oxy)-phenyl]-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 1-{4-[3-(diethylamino)propoxy]phenyl}ethanone (2.3 mmol) in anhydrous MeOH (5 mL) at 0° C., pyrrolidone hydrotribromide (1.2 eq., 2.7 mmol) was added, according to General Procedure R1. The reaction mixture was stirred under nitrogen at 0° C. for 1 h and was allowed to warm to rt until completion, as indicated by TLC or HPLC. The solvent was then removed in vacuuo and the crude 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone was used for further transformation. To a stirred solution of 4-(4-methoxy-naphthalen-1-yloxy)aniline (1.2 eq., 2.5 mmol) in anhydrous DMF (5 mL) DIEA (3 eq. 7.5 mmol) was added, followed by slow addition of the 2-bromo-1-{4-[3-(diethylamino)propoxy]phenyl}ethanone described above (2.3 mmol), according to General Procedure R2. The reaction mixture was stirred under nitrogen at rt until completion, as indicated by TLC or HPLC. The reaction mixture was then diluted with cold H2O and the product was isolated in EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of solvent in vacuuo afforded the desired product. The crude alkylated aniline was used for further transformation.

Aufarbeitung

  1. temperatureto warm to rt until completion
  2. customThe solvent was then removed in vacuuo
  3. stirringThe reaction mixture was stirred under nitrogen at rt until completion
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of solvent in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-2c9d9c510ffd4b41910619c6875df482
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361678B2

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