phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate

Base Information

• Chemical Name: phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate
• CAS No.: 261895-24-3
• Molecular Formula: C₂₆H₂₈N₂O₂
• Molecular Weight: 400.521
• Mol file: 261895-24-3.mol

Synonyms:phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate

Chemical Property of phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate

There total 4 articles about phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-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: 68.0%

1-methylindole (603-76-9) + N-(2-bromobut-2-enyl)-N-pent-3-ynyl(phenylmethoxy)carboxamide (260430-49-7) → phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate (261895-24-3)

Guidance literature:

1-methylindole; With tert.-butyl lithium; In tetrahydrofuran;

With triethyl borane; In tetrahydrofuran;

N-(2-bromobut-2-enyl)-N-pent-3-ynyl(phenylmethoxy)carboxamide; With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 60 ℃;

DOI:10.1016/S0040-4020(99)01016-9

Reference yield:

pent-3-ynyl triflate (54106-83-1) → phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate (261895-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 9.9 g / diisopropylethylamine / CH₂Cl₂ / 20 °C

2.1: 78 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

3.1: tert-butyllithium / tetrahydrofuran

3.2: triethylborane / tetrahydrofuran

3.3: 68 percent / PdCl₂(PPh₃)2 / tetrahydrofuran / 60 °C

With tert.-butyl lithium; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Alkylation / 2.1: Acylation / 3.1: Metallation / 3.2: Substitution / 3.3: Cyclization;

DOI:10.1016/S0040-4020(99)01016-9

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → phenylmethyl 3-ethylidene-4-[(1-methylindol-2-yl)ethylidene]piperidine-1-carboxylate (261895-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

2.1: tert-butyllithium / tetrahydrofuran

2.2: triethylborane / tetrahydrofuran

2.3: 68 percent / PdCl₂(PPh₃)2 / tetrahydrofuran / 60 °C

With tert.-butyl lithium; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Acylation / 2.1: Metallation / 2.2: Substitution / 2.3: Cyclization;

DOI:10.1016/S0040-4020(99)01016-9

upstream raw materials:

1-methylindole

N-(2-bromobut-2-enyl)-N-pent-3-ynyl(phenylmethoxy)carboxamide

pent-3-ynyl triflate

benzyl chloroformate

Downstream raw materials:

phenylmethyl 5,6,11-trimethyl-1,2,3,4-tetrahydropyrido[4,3-b]carbazole-2-carboxylate