methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate

Base Information

• Chemical Name: methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate
• CAS No.: 729614-30-6
• Molecular Formula: C₂₂H₂₃NO₂
• Molecular Weight: 333.43
• Mol file: 729614-30-6.mol

Synonyms:methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate

Chemical Property of methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate

There total 6 articles about methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate 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: 81.0%

methyl 5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate (729613-74-5) + benzyl bromide (100-39-0) → methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate (729614-30-6)

Guidance literature:

methyl 5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate; With potassium hydroxide; In dimethyl sulfoxide; for 0.0833333h;

benzyl bromide; In dimethyl sulfoxide; for 0.166667h;

Reference yield: 51.0%

methyl 1-benzyl-3-iodo-1H-indole-7-carboxylate (1027787-38-7) + 5-(5- bromopentyl)-1-aza-5-germabicyclo[3.3.3]undecane → methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate (729614-30-6)

Guidance literature:

With norborn-2-ene; caesium carbonate; palladium(II) bromide; tris(para-trifluoromethyl)phenyl phosphine; In para-xylene; acetonitrile; at 130 ℃; for 14h; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0040-1720693

Reference yield:

1,3-dioxoisoindolin-2-yl 6-bromohexanoate → methyl 5-benzyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate (729614-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Schlenk technique

2: palladium(II) bromide; caesium carbonate; norborn-2-ene; tris(para-trifluoromethyl)phenyl phosphine / acetonitrile; para-xylene / 14 h / 130 °C / Inert atmosphere; Schlenk technique

With norborn-2-ene; caesium carbonate; palladium(II) bromide; zinc; tris(para-trifluoromethyl)phenyl phosphine; In para-xylene; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-0040-1720693

upstream raw materials:

methyl 5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate

benzyl bromide

methyl 1H-indole-7-carboxylate

methyl 1-benzyl-3-iodo-1H-indole-7-carboxylate

Downstream raw materials:

methyl 5-benzyl-10-oxo-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylate

Refernces

• 1、 Barf, Tjeerd,Lehmann, Fredrik,Hammer, Kristin,Haile, Saba,Axen, Eva,Medina, Carmen,Uppenberg, Jonas,Svensson, Stefan,Rondahl, Lena,Lundbaeck, Thomas. "N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors". scheme or table. p. 1745 - 1748. Retrieved 2010/02/28.