dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate

Base Information

• Chemical Name: dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate
• CAS No.: 1478648-89-3
• Molecular Formula: C₂₅H₂₆N₂O₆S
• Molecular Weight: 482.557
• Mol file: 1478648-89-3.mol

Synonyms:dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate

Chemical Property of dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate

There total 6 articles about dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate 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: 70.0%

dimethyl 2-(2-(2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)ethyl)malonate (1478648-84-8) → dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate (1478648-89-3)

Guidance literature:

dimethyl 2-(2-(2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)ethyl)malonate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

With iodine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0036-1592002

Reference yield:

formyl-4 methoxycarbonyl-2 butanoate de methyle (72473-15-5) → dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate (1478648-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / 20 °C

2.1: triethylamine / dichloromethane / 12 h / 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C

3.2: 0.17 h / 20 °C

With acetic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: |Pictet-Spengler Synthesis;

DOI:10.1055/s-0033-1339472

Reference yield:

tryptamine (61-54-1) → dimethyl 3-tosyl-3,3a,4,5-tetrahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-6,6(2H)-dicarboxylate (1478648-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; water / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetic acid;

DOI:10.1055/s-0036-1592002

upstream raw materials:

dimethyl 2-(2-(2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)ethyl)malonate

C₁₈H₂₂N₂O₄

p-toluenesulfonyl chloride

malonic acid dimethyl ester