4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide

Base Information

• Chemical Name: 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide
• CAS No.: 1093256-13-3
• Molecular Formula: C₂₁H₁₇BrClFN₄O₂
• Molecular Weight: 491.747

Synonyms:4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide

Chemical Property of 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide

Chemical Property:

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Technology Process of 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide

There total 9 articles about 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide 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: 63.1%

4-bromo-2-methyl-1H-imidazole-5-carboxylic acid (1093261-50-7) + 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-ethylbenzonitrile (1093262-38-4) → 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (1093256-13-3)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25 ℃;

Reference yield:

3-bromo-5-fluorobenzonitrile (179898-34-1) → 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (1093256-13-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran; dimethyl sulfoxide / 0.25 h / 20 °C

1.2: 20 h / 125 °C

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux

3.1: sodium azide / dimethyl sulfoxide / 25 °C

4.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 25 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; n-heptane / 2 h / 70 °C / Inert atmosphere

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 25 °C

With N-Bromosuccinimide; sodium azide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; n-heptane; dimethyl sulfoxide;

Reference yield:

6-chloro-2-fluoro-3-methylphenol (261762-91-8) → 4-bromo-N-({4-chloro-3-[(3-cyano-5-ethylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (1093256-13-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran; dimethyl sulfoxide / 0.25 h / 20 °C

1.2: 20 h / 125 °C

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / Reflux

3.1: sodium azide / dimethyl sulfoxide / 25 °C

4.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 25 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; n-heptane / 2 h / 70 °C / Inert atmosphere

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 25 °C

With N-Bromosuccinimide; sodium azide; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; n-heptane; dimethyl sulfoxide;

upstream raw materials:

3-bromo-5-fluorobenzonitrile

5-bromo-2-methyl-1⁽³⁾H-imidazole-4-carbaldehyde

6-chloro-2-fluoro-3-methylphenol

2-methylimidazole-4⁽⁵⁾-carbaldehyde

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