Acetonitrile → 2-[3-(4'-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol

HRID 923266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923266
C([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C.Br[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1>C(Cl)Cl>[F:45][C:42]1[CH:43]=[CH:44][C:39]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][N:22]2[C:23]([CH2:25][CH2:26][OH:27])=[CH:24][N:20]=[CH:21]2)=[CH:40][CH:41]=1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanolHCID 114484672-Bromomethyl-4'-fluorobiphenyl

Produkt 1

HCID 668864042-[3-(4'-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 2-(1-trityl-1H-imidazol-4-yl)ethanol (0.65 g, 1.80 mmol), acetonitrile (9 mL) and CH2Cl2 (12 mL) is added a solution of 2-bromomethyl-4′-fluorobiphenyl (0.478 g, 1.80 mmol) in CH2Cl2 (2 mL). The resulting mixture is stirred at room temperature overnight. The solution is concentrated and the residue is taken up in MeOH and heated to 75° C. for 3.5 h. The solution is then concentrated and the residue is partitioned between CH2Cl2 and aqueous 5% NaHCO3. The aqueous layer is then extracted with CH2Cl2 (3×). The combined organic layers are then washed with brine and dried over Na2SO4. The residue is then purified by flash chromatography (CH2Cl2/MeOH) give 2-[3-(4′-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol. MS (ESI) m/z 297.1 (M+H).

Aufarbeitung

  1. concentrationThe solution is concentrated
  2. temperatureheated to 75° C. for 3.5 h
  3. concentrationThe solution is then concentrated
  4. customthe residue is partitioned between CH2Cl2 and aqueous 5% NaHCO3
  5. extractionThe aqueous layer is then extracted with CH2Cl2 (3×)
  6. washThe combined organic layers are then washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe residue is then purified by flash chromatography (CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-6f4968c2561d40c8a108c1c6a0a90ab5
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278969B2

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