N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide

Base Information

• Chemical Name: N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide
• CAS No.: 1529806-81-2
• Molecular Formula: C₃₂H₃₃N₃O₄S₂
• Molecular Weight: 587.764
• Mol file: 1529806-81-2.mol

Synonyms:N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide

Chemical Property of N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide

There total 14 articles about N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide 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:

N-((1-allylindol-2-yl)methyl)-4-methylbenzenesulfonamide (1262779-18-9) + 3-(2-methyl-1-tosylaziridin-2-yl)prop-2-yn-1-ol (1584210-03-6) → N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide (1529806-81-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; Inert atmosphere;

DOI:10.1016/j.tet.2013.11.084

Reference yield:

α-Azidozimtsaeuremethylester (94413-73-7) → N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide (1529806-81-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 5,5-dimethyl-1,3-cyclohexadiene / 1 h / Reflux; Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C

2.2: 1 h / 0 - 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

4.1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere

5.1: titanium(IV) tetraethanolate / toluene / 4 h / Reflux

6.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / 0 - 20 °C

7.1: triphenylphosphine; diethylazodicarboxylate / toluene / Inert atmosphere

With manganese(IV) oxide; titanium(IV) tetraethanolate; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide; toluene; mineral oil; 7.1: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2013.11.084

Reference yield:

1-allyl-2-(hydroxymethyl)indole (284049-55-4) → N-((1-allyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide (1529806-81-2)

Guidance literature:

Multi-step reaction with 4 steps

1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere

2: titanium(IV) tetraethanolate / toluene / 4 h / Reflux

3: sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / 0 - 20 °C

4: triphenylphosphine; diethylazodicarboxylate / toluene / Inert atmosphere

With manganese(IV) oxide; titanium(IV) tetraethanolate; sodium tetrahydroborate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 4: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2013.11.084

upstream raw materials:

benzaldehyde

α-Azidozimtsaeuremethylester

indole-2-carboxylic acid methyl ester

1-allyl-1H-indole-2-carboxylic acid methyl ester

Downstream raw materials:

9-allyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole]