methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate

Base Information

• Chemical Name: methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate
• CAS No.: 1351377-85-9
• Molecular Formula: C₁₇H₁₆F₃NO₂
• Molecular Weight: 323.315

Synonyms:methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate

Chemical Property of methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate

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Technology Process of methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate

There total 2 articles about methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate 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: 82.0%

iodobenzene (591-50-4) + methyl 2-[methyl(prop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate (1309440-86-5) → methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate (1351377-85-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0030-1261217

Reference yield:

N-methyl-N,N-dipropargylamine (2568-61-8) → methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate (1351377-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: [copper(II)(trifluoroacetylacetonate)₂] / toluene / 100 °C / Inert atmosphere

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; [copper(II)(trifluoroacetylacetonate)₂]; triethylamine; In N,N-dimethyl-formamide; toluene; 2: Sonogashira coupling;

DOI:10.1055/s-0030-1261217

Reference yield: 80.0%

methyl 2-[methyl(3-phenylprop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate (1351377-85-9) → methyl 3-methyl-8-phenyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1(8),5-diene-4-carboxylate (1351377-95-1)

Guidance literature:

In toluene; at 110 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1261217

upstream raw materials:

iodobenzene

methyl 2-[methyl(prop-2-yn-1-yl)amino]-2-(trifluoromethyl)penta-3,4-dienoate

N-methyl-N,N-dipropargylamine

Downstream raw materials:

methyl 3-methyl-8-phenyl-4-(trifluoromethyl)-3-azabicyclo[4.2.0]octa-1⁽⁸⁾,5-diene-4-carboxylate

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