Acetonitrile → Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 51816

Reaktionsgleichung

Reaktionsgleichung von HRID 51816
BrCC1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:5][C:4]=1C(C)C.[C:25]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=O)[CH3:26].[C:33]([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]#N>O>[N:28]1([C:25]2[CH:4]=[CH:5][C:6]([C:9]#[C:10][C:11]3[CH:12]=[CH:13][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=3)=[C:7]([CH3:8])[C:26]=2[CH:40]([CH3:39])[CH3:33])[CH:32]=[CH:31][N:30]=[CH:29]1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 86585936Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate2×

Produkt 1

HCID 86585935Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate (Intermediate 156, 72.0 mg, 0.19 mmol) and 1-acetylimidazole (22.0 mg, 0.20 mmol) in 5 mL CH3CN was heated at 65° C. for 8 h and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (0.5% Et3N in 5% MeOH-EtOAc) afforded 40.0 mg (58%) of the title compound as a colorless solid.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-391d15777b1f4f13a57996ab186abac1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713647B2

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