1,1'-Carbonyldiimidazole → 2-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

HRID 1054080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054080
[CH3:1][CH:2]([CH3:17])[CH:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[OH:4].[CH:18]1[N:22]=[CH:21][N:20]([C:23](N2C=NC=C2)=[O:24])[CH:19]=1>C(#N)C>[N:20]1([C:23]([O:4][CH:3]([C:5]2[CH:6]=[N:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)[CH:2]([CH3:17])[CH3:1])=[O:24])[CH:19]=[CH:18][N:22]=[CH:21]1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 675104242-Methyl-1-(6-phenylpyridin-3-yl)propan-1-ol

Produkt 1

HCID 573298692-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Synthesized using compound 43a (81 mg, 0.36 mmol), CDI (289 mg, 1.78 mmol) and acetonitrile (5 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (4:1) as eluent. White solid. Yield: 90.0 mg, 90%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.95 (d, J=6.9 Hz, 3H), 1.14 (d, J=6.6 Hz, 3H), 2.37 (m, 1H), 5.70 (d, J=8.2 Hz, 1H), 7.09 (dd, J=1.6, 0.6 Hz, 1H), 7.40-7.51 (m, 4H), 7.72-7.79 (m, 2H), 7.98-8.03 (m, 2H), 8.19 (t, J=0.9 Hz, 1H), 8.71 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.7, 18.8, 33.6, 83.7, 117.2, 120.4, 127.1, 129.0, 129.5, 131.1, 131.8, 135.6, 137.2, 138.8, 148.7, 158.0; MS (ESI): m/z=322.32 [M+H]+.

Aufarbeitung

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (4:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-2aa067969fb74bc88e9aaaa3bbdb9864
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394290B2

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