5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid

Base Information

• Chemical Name: 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid
• CAS No.: 1352240-46-0
• Molecular Formula: C₂₆H₂₂F₂N₂O₃
• Molecular Weight: 448.469
• Mol file: 1352240-46-0.mol

Synonyms:5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid

Chemical Property of 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid

There total 7 articles about 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic 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: 52.0%

N-ethyl-2-{2-[(4aR,5R)-1-(4-fluorophenyl)-4,5-dihydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}benzamide (1352240-43-7) → 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid (1352240-46-0)

Guidance literature:

With sodium bismuthate; acetic acid; In water; acetone; for 0.5h; Reflux;

DOI:10.1016/j.bmc.2011.10.054

Reference yield:

(4aS,5R)-5-ethynyl-1-(4-fluorophenyl)-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-ol (754235-83-1) → 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid (1352240-46-0)

Guidance literature:

Multi-step reaction with 6 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / tetrahydrofuran / 1 h / 20 - 80 °C

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C

3: water; sodium hydroxide / ethanol / 1 h / 100 °C

4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C

5: CYP₃A₄ bioreactor / Microbiological reaction; Enzymatic reaction

6: sodium bismuthate; acetic acid / water; acetone / 0.5 h / Reflux

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium bismuthate; palladium 10% on activated carbon; water; hydrogen; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 1: Sonogashira coupling;

DOI:10.1016/j.bmc.2011.10.054

Reference yield:

methyl 2-fluoro-6-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate (1352240-27-7) → 5-fluoro-2-{5-[1-(4-fluorophenyl)-5-methyl-1H-indazol-6-yl]-3-oxopentyl}benzoic acid (1352240-46-0)

Guidance literature:

Multi-step reaction with 5 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C

2: water; sodium hydroxide / ethanol / 1 h / 100 °C

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C

4: CYP₃A₄ bioreactor / Microbiological reaction; Enzymatic reaction

5: sodium bismuthate; acetic acid / water; acetone / 0.5 h / Reflux

With sodium bismuthate; palladium 10% on activated carbon; water; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2011.10.054

upstream raw materials:

(4aS,5R)-5-ethynyl-1-(4-fluorophenyl)-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-ol

methyl 2-fluoro-6-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate

methyl 2-fluoro-6-{2-[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}benzoate

2-fluoro-6-{2-[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}benzoic acid