5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid

Base Information

• Chemical Name: 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid
• CAS No.: 1219737-12-8
• Molecular Formula: C₂₇H₁₉ClN₂O₃
• Molecular Weight: 454.912

Synonyms:5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid

Chemical Property of 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid

Chemical Property:

• Boiling Point: 712.6±70.0 °C(Predicted)
• Density: 1.349±0.06 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

MK-3903 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: MK-3903 is a potent and selective AMP-activated protein kinase (AMPK) activator with an EC50 of 8 nM.

Technology Process of 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid

There total 9 articles about 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid 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:

methyl 5-[(5-biphenyl-4-yl-6-chloro-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate (1219741-57-7) → 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid (1219737-12-8)

Guidance literature:

methyl 5-[(5-biphenyl-4-yl-6-chloro-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate; With water; sodium hydroxide; In methanol; at 70 ℃; for 1h;

With hydrogenchloride; In methanol; water;

Reference yield:

5-chloro-2-nitroaniline (1635-61-6) → 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid (1219737-12-8)

Guidance literature:

Multi-step reaction with 8 steps

1: acetic acid; N-iodo-succinimide / 50 °C

2: iron; ammonium chloride / ethanol; water / 50 °C / Inert atmosphere

3: potassium hydroxide / ethanol / 3 h / Reflux

4: potassium carbonate / acetone / 1 h / 0 - 20 °C

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 0.17 h / 120 °C / Microwave irradiation

7: neat (no solvent) / 3 h / 130 °C / Inert atmosphere; Sealed tube

8: sodium hydroxide / water; methanol / 1 h / 70 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron; potassium carbonate; ammonium chloride; acetic acid; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; sodium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/acs.jmedchem.7b01344

Reference yield:

2-nitro-4-iodo-5-chloroaniline (335349-57-0) → 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid (1219737-12-8)

Guidance literature:

Multi-step reaction with 7 steps

1: iron; ammonium chloride / ethanol; water / 50 °C / Inert atmosphere

2: potassium hydroxide / ethanol / 3 h / Reflux

3: potassium carbonate / acetone / 1 h / 0 - 20 °C

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 0.17 h / 120 °C / Microwave irradiation

6: neat (no solvent) / 3 h / 130 °C / Inert atmosphere; Sealed tube

7: sodium hydroxide / water; methanol / 1 h / 70 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron; potassium carbonate; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; sodium hydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/acs.jmedchem.7b01344

upstream raw materials:

methyl 5-[(5-biphenyl-4-yl-6-chloro-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate

5-chloro-2-nitroaniline

2-nitro-4-iodo-5-chloroaniline

2, 4-chloro-5-iodobenzene-1,2-diamine

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