ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate

Base Information

• Chemical Name: ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate
• CAS No.: 1352240-25-5
• Molecular Formula: C₂₈H₂₅FN₂O₃
• Molecular Weight: 456.517
• Mol file: 1352240-25-5.mol

Synonyms:ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate

Chemical Property of ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate

There total 2 articles about ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate 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: 91.0%

(4aS,5R)-5-ethynyl-1-(4-fluorophenyl)-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-ol (754235-83-1) → ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate (1352240-25-5)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine; In tetrahydrofuran; at 20 - 80 ℃; for 1h;

DOI:10.1016/j.bmc.2011.10.054

Reference yield:

4-fluorophenyhydrazine hydrochloride (823-85-8) → ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate (1352240-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate; acetic acid / 1 h / 20 °C

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

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; acetic acid; diisopropylamine; In tetrahydrofuran; 2: Sonogashira coupling;

DOI:10.1016/j.bmc.2011.10.054

Reference yield: 91.0%

ethyl 3-{[(4aS,5R)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethynyl}benzoate (1352240-25-5) → ethyl 3-{2-[(4aS,5S)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}benzoate (1352240-29-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃;

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

4-fluorophenyhydrazine hydrochloride

Downstream raw materials:

ethyl 3-{2-[(4aS,5S)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}benzoate

3-{2-[(4aS,5S)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}benzoic acid

3-{2-[(4aS,5S)-1-(4-fluorophenyl)-5-hydroxy-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-yl]ethyl}-N-methylbenzamide