(E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate

Base Information

• Chemical Name: (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate
• CAS No.: 1369853-06-4
• Molecular Formula: C₂₅H₂₅F₃N₂O₅
• Molecular Weight: 490.479
• Mol file: 1369853-06-4.mol

Synonyms:(E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate

Chemical Property of (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate

There total 6 articles about (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate 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: 91.0%

(E)-N-{2-[1-benzyl-2-(3-hydroxyprop-1-en-1-yl)-5-methoxy-1H-indol-3-yl]ethyl}-2,2,2-trifluoroacetamide (1369852-97-0) + methyl chloroformate (79-22-1) → (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate (1369853-06-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 21 ℃; for 16h; Inert atmosphere;

DOI:10.1055/s-0031-1289656

Reference yield:

N-[2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethyl]-2,2,2-trifluoroacetamide (1369852-63-0) → (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate (1369853-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / diethyl ether; hexane / 2 h / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 16 h / 75 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 16 h / 0 - 21 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; lithium chloride; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Stille coupling;

DOI:10.1055/s-0031-1289656

Reference yield:

N-[2-(1-benzyl-2-iodo-5-methoxy-1H-indol-3-yl)ethyl]-2,2,2-trifluoroacetamide (1369852-86-7) → (E)-3-{1-benzyl-5-methoxy-3-[2-(2,2,2-trifluoroacetamido)ethyl]-1H-indol-2-yl}allyl methyl carbonate (1369853-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 16 h / 75 °C / Inert atmosphere

2: pyridine / dichloromethane / 16 h / 0 - 21 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; lithium chloride; In dichloromethane; N,N-dimethyl-formamide; 1: Stille coupling;

DOI:10.1055/s-0031-1289656

upstream raw materials:

N-[2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethyl]-2,2,2-trifluoroacetamide

N-[2-(1-benzyl-2-iodo-5-methoxy-1H-indol-3-yl)ethyl]-2,2,2-trifluoroacetamide

(E)-N-{2-[1-benzyl-2-(3-hydroxyprop-1-en-1-yl)-5-methoxy-1H-indol-3-yl]ethyl}-2,2,2-trifluoroacetamide

methyl chloroformate

Downstream raw materials:

1-{9-benzyl-6-methoxy-1-vinyl-3,4-dihydro-1H-pyrido[3,4-b]indol-2(9H)-yl}-2,2,2-trifluoroethanone