11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide

Base Information

• Chemical Name: 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide
• CAS No.: 902148-53-2
• Molecular Formula: C₂₅H₂₉N₃O₅S
• Molecular Weight: 483.588
• Mol file: 902148-53-2.mol

Synonyms:11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide

Chemical Property of 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide

There total 3 articles about 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide 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: 88.0%

2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-1H-indole-6-carboxamide (902148-40-7) + 2-formyl-4-methoxyphenylboronic acid (139962-95-1) → 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide (902148-53-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride; In ethanol; toluene;

DOI:10.1021/acs.oprd.8b00214

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide (902148-53-2)

Guidance literature:

Multi-step reaction with 5 steps

1: trifluoroacetic acid; triethylsilane / toluene / 1.5 h / 0 - 30 °C / Inert atmosphere; Large scale

2: acetic acid; bromine

3: sodium hydroxide / methanol; tetrahydrofuran

4: 1,1'-carbonyldiimidazole / tetrahydrofuran

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; sodium carbonate / toluene; ethanol

With triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; sodium carbonate; acetic acid; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium chloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/acs.oprd.8b00214

Reference yield:

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8) → 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide (902148-53-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / methanol; tetrahydrofuran

2: 1,1'-carbonyldiimidazole / tetrahydrofuran

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; sodium carbonate / toluene; ethanol

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; 1,1'-carbonyldiimidazole; lithium chloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/acs.oprd.8b00214

upstream raw materials:

2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-1H-indole-6-carboxamide

2-formyl-4-methoxyphenylboronic acid

cyclohexanone

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Downstream raw materials:

cycloprop[d]indolo[2,1-a][2]benzazepine-1a(2H)-carboxylic acid, 8-cyclohexyl-5-[[[(dimethylamino)sulfonyl]amino]carbonyl]-1,12b-dihydro-11-methoxy-, (+/-)-

cycloprop[d]indolo[2,1-a][2]benzazepine-1a(2H)-carboxylic acid, 8-cyclohexyl-5-[[[(dimethylamino)sulfonyl]amino]carbonyl]-1,12b-dihydro-11-methoxy-, methyl ester, (+/-)-

1,1-dimethylethyl (8-cyclohexyl-5-((((dimethylamino)sulfonyl)amino)carbonyl)-11-(methyloxy)-1,12b-dihydrocyclopropa[d]indolo[2,1-a][2]benzazepin-1a(2H)-yl)carbamate

1a-amino-8-cyclohexyl-N-((dimethylamino)sulfonyl)-11-(methyloxy)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide hydrochloride