ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate

Base Information

• Chemical Name: ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate
• CAS No.: 1361403-92-0
• Molecular Formula: C₂₄H₂₀N₂O₄
• Molecular Weight: 400.434
• Mol file: 1361403-92-0.mol

Synonyms:ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate

Chemical Property of ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate

There total 4 articles about ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-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: 93.0%

ethyl (E)-2-(1-benzyl-2-oxoindolin-3-ylidene)-2-cyanoacetate (26960-51-0) + methyl ethynyl ketone (1423-60-5) → ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate (1361403-92-0)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2012.01.036

Reference yield:

ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate (14003-18-0,14003-19-1,59225-18-2) → ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate (1361403-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: triphenylphosphine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

With potassium carbonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.01.036

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → ethyl 3-acetyl-9-benzyl-4-cyano-4,9-dihydropyrano[2,3-b]indole-4-carboxylate (1361403-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine / ethanol / 2 h / Reflux; Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: triphenylphosphine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

With piperidine; potassium carbonate; triphenylphosphine; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.01.036

upstream raw materials:

ethyl 2-(2-oxoindolin-3-ylidene)cyanoacetate

indole-2,3-dione

ethyl (E)-2-(1-benzyl-2-oxoindolin-3-ylidene)-2-cyanoacetate

methyl ethynyl ketone