alpha-(4-Fluorophenyl)-alpha-[4-(4-pyridyl)phenyl]-1H-imidazole-1-ethanol

Base Information

• Chemical Name: alpha-(4-Fluorophenyl)-alpha-[4-(4-pyridyl)phenyl]-1H-imidazole-1-ethanol
• CAS No.: 137103-53-8
• Molecular Formula: C22H18FN3O
• Molecular Weight: 359.403
• DSSTox Substance ID: DTXSID00875356
• Nikkaji Number: J491.813D
• ChEMBL ID: CHEMBL321024

Synonyms:CHEMBL321024;137103-53-8;SCHEMBL9202252;DTXSID00875356;BDBM50004676;1H-IMIDAZOLE-1-ETHANOL, _-(4-FLUOROPHENYL)-_-[4-;1-(4-Fluoro-phenyl)-2-imidazol-1-yl-1-(4-pyridin-4-yl-phenyl)-ethanol;alpha-(4-Fluorophenyl)-alpha-[4-(4-pyridyl)phenyl]-1H-imidazole-1-ethanol

Chemical Property of alpha-(4-Fluorophenyl)-alpha-[4-(4-pyridyl)phenyl]-1H-imidazole-1-ethanol

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 359.14339037
• Heavy Atom Count: 27
• Complexity: 457

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC=NC=C2)C(CN3C=CN=C3)(C4=CC=C(C=C4)F)O

Technology Process of alpha-(4-Fluorophenyl)-alpha-[4-(4-pyridyl)phenyl]-1H-imidazole-1-ethanol

There total 9 articles about alpha-(4-Fluorophenyl)-alpha-[4-(4-pyridyl)phenyl]-1H-imidazole-1-ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1H-imidazole (288-32-4) + Methanesulfonic acid 2-(4-fluoro-phenyl)-2-hydroxy-2-(4-pyridin-4-yl-phenyl)-ethyl ester (137103-84-5) → 1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-2-(1-imidazolyl)-1-ethanol (137103-53-8)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 95 ℃; for 18h; Yield given;

DOI:10.1021/jm00095a009

Reference yield:

4-bromopyridin (1120-87-2) → 1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-2-(1-imidazolyl)-1-ethanol (137103-53-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) ZnCl₂, 3.) Ni(PPh₃)2Cl₂, DIBAL-H, 4.) HCl

2: 90 percent / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 23 deg C, 30 min

3: 78 percent / p-TsOH / CHCl₃ / 80 °C / Heating

4: 66 percent / N-methylmorpholine N-oxide, OsO₄, pyridine / acetone; H₂O / 40 h / Heating

5: Et₃N / CH₂Cl₂ / 0.5 h

6: t-BuOK / dimethylformamide / 18 h / 95 °C

With pyridine; hydrogenchloride; osmium(VIII) oxide; bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; zinc(II) chloride; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00095a009

Reference yield:

2-(4-Bromophenyl)-2,2-dimethoxyethane (53578-00-0) → 1-(4-fluorophenyl)-1-<4-(4-pyridyl)phenyl>-2-(1-imidazolyl)-1-ethanol (137103-53-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) ZnCl₂, 3.) Ni(PPh₃)2Cl₂, DIBAL-H, 4.) HCl

2: 90 percent / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 23 deg C, 30 min

3: 78 percent / p-TsOH / CHCl₃ / 80 °C / Heating

4: 66 percent / N-methylmorpholine N-oxide, OsO₄, pyridine / acetone; H₂O / 40 h / Heating

5: Et₃N / CH₂Cl₂ / 0.5 h

6: t-BuOK / dimethylformamide / 18 h / 95 °C

With pyridine; hydrogenchloride; osmium(VIII) oxide; bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; zinc(II) chloride; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00095a009

upstream raw materials:

1H-imidazole

Methanesulfonic acid 2-(4-fluoro-phenyl)-2-hydroxy-2-(4-pyridin-4-yl-phenyl)-ethyl ester

4-bromopyridin

2-(4-Bromophenyl)-2,2-dimethoxyethane

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