12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester

Base Information

• Chemical Name: 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester
• CAS No.: 877278-03-0
• Molecular Formula: C₂₈H₃₇N₃O₃Si
• Molecular Weight: 491.706
• Mol file: 877278-03-0.mol

Synonyms:12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester

Chemical Property of 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester

There total 5 articles about 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester 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: 64.0%

3-cyclohexyl-2-[4-ethenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazol-5-yl]-1-(2-propenyl)-1H-indole-6-carboxylic acid methyl ester (877277-95-7) → 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester (877278-03-0)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; for 8h; Heating / reflux;

Reference yield:

3-cyclohexyl-2-[4-ethenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazol-5-yl]-1H-indole-6-carboxylic acid methyl ester (877277-88-8) → 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester (877278-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydride

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium hydride; In dichloromethane;

DOI:10.1016/j.bmcl.2012.02.063

Reference yield:

3-cyclohexyl-2-[4-iodo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazol-5-yl]-1H-indole-6-carboxylic acid methyl ester (877277-80-0) → 12-cyclohexyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester (877278-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 100 °C

2: potassium hydride

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis-triphenylphosphine-palladium(II) chloride; potassium hydride; lithium chloride; In dichloromethane; N,N-dimethyl-formamide; 1: Stille coupling;

DOI:10.1016/j.bmcl.2012.02.063

upstream raw materials:

3-cyclohexyl-2-[4-ethenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazol-5-yl]-1-(2-propenyl)-1H-indole-6-carboxylic acid methyl ester

3-cyclohexyl-2-[4-iodo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazol-5-yl]-1H-indole-6-carboxylic acid methyl ester

3-cyclohexyl-2-[4-ethenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazol-5-yl]-1H-indole-6-carboxylic acid methyl ester

(2-trimethylethylsilylethoxy)methyl chloride

Downstream raw materials:

12-cyclohexyl-1,4,5,6-tetrahydro-1-[[2-(trimethylsilyl)ethoxy]methyl]-imidazo[4',5':3,4]azepino[1,2-a]indole-9-carboxylic acid methyl ester