methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate

Base Information

• Chemical Name: methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate
• CAS No.: 1434004-01-9
• Molecular Formula: C₂₈H₂₆N₆O₇
• Molecular Weight: 558.55

Synonyms:methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate

Chemical Property of methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate

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Technology Process of methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate

There total 2 articles about methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-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: 59.0%

methyl 2-(4-methoxybenzyl)hydrazinecarboxylate (1383604-52-1) + ethyl 3-azido-4-ethynylbenzoate (1434003-91-4) + 4-nitrobenzaldehdye (555-16-8) → methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate (1434004-01-9)

Guidance literature:

With [AuCl(IPr)]; silver(I) triflimide; In 1,2-dichloro-ethane; at 50 ℃; Inert atmosphere;

DOI:10.1039/c3ob40223a

Reference yield:

C11H11NO2 (1260650-82-5) → methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate (1434004-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium nitrite; sulfuric acid / water; acetonitrile; N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 0.5 h / 0 - 20 °C

2.1: [AuCl(IPr)]; silver(I) triflimide / 1,2-dichloro-ethane / 50 °C / Inert atmosphere

With sulfuric acid; [AuCl(IPr)]; silver(I) triflimide; sodium nitrite; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c3ob40223a

Reference yield: 72.0%

methyl 5-[2-azido-4-(ethoxycarbonyl)phenyl]-2-(4-methoxybenzyl)-3-(4-nitrophenyl)-2,3-dihydro-1H-pyrazole-1-carboxylate (1434004-01-9) → 6-ethyl 1-methyl 2-(4-methoxybenzyl)-3-(4-nitrophenyl)-1,2,3,4-tetrahydropyrazolo[4,3-b]indole-1,6-dicarboxylate (1434004-12-2)

Guidance literature:

With rhodium(III) chloride hydrate; In 1,2-dimethoxyethane; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c3ob40223a

upstream raw materials:

methyl 2-(4-methoxybenzyl)hydrazinecarboxylate

ethyl 3-azido-4-ethynylbenzoate

4-nitrobenzaldehdye

C₁₁H₁₁NO₂

Downstream raw materials:

6-ethyl 1-methyl 2-(4-methoxybenzyl)-3-(4-nitrophenyl)-1,2,3,4-tetrahydropyrazolo[4,3-b]indole-1,6-dicarboxylate

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