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

HRID 76885Notes

Reaction equation

HRID 76885 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-deba95d6e0b3463e83bf8667bbefda2a
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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