Imidazole → HCID 68193314, compound

HRID 1626829Notes

Reaction equation

HRID 1626829 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@@H:15]([OH:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CN=C1.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24].C(OCC)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([CH3:16])[O:17][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 68193299HCID 68193299, compound

Product 1

HCID 68193314HCID 68193314, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S)-1-(4′-Bromobiphenyl-4-yl)propan-2-ol (0.23 g, 0.79 mmol) and imidazole (0.11 g, 1.6 mmol) were dissolved in N,N-dimethylformamide (5 mL), and tert-butyldimethylchlorosilane (0.24 g, 1.6 mmol) was added under a nitrogen atmosphere, followed by stirring at room temperature for 1 hour. Diethyl ether was added to the reaction solution, followed by sequential washing with water and hydrochloric acid (1 M). After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.80 (hexane/ethyl acetate=10/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.25 g, 0.62 mmol) as a white solid (yield 78%).

Workup

  1. washby sequential washing with water and hydrochloric acid (1 M)
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.80 (hexane/ethyl acetate=10/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8160561045ce40a6a243dad73c223ac5
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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