3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid

Base Information

• Chemical Name: 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid
• CAS No.: 1311158-04-9
• Molecular Formula: C₂₃H₂₁N₃O₆
• Molecular Weight: 435.436

Synonyms:3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid

Chemical Property of 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid

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Technology Process of 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid

There total 4 articles about 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid 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 1-(3,4-dimethoxybenzyl)-3-[1-(2-ethoxy-2-oxoethyl)-1H-indol-3-yl]-1H-pyrazole-5-carboxylate (1311157-93-3) → 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid (1311158-04-9)

Guidance literature:

ethyl 1-(3,4-dimethoxybenzyl)-3-[1-(2-ethoxy-2-oxoethyl)-1H-indol-3-yl]-1H-pyrazole-5-carboxylate; With sodium hydroxide; In ethanol; water; Reflux;

With hydrogenchloride; In ethanol; water; pH=3;

DOI:10.1007/s12272-011-0301-2

Reference yield:

3-acetylindole (703-80-0) → 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid (1311158-04-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium ethanolate / 2 h / 75 °C

2.1: hydrazine hydrate; acetic acid / isopropyl alcohol / 2 h / Cooling

3.1: potassium bromide; potassium hydroxide / dimethyl sulfoxide / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 10 °C

4.2: 20 °C

5.1: sodium hydroxide / ethanol; water / Reflux

5.2: pH 3

With sodium ethanolate; sodium hydride; hydrazine hydrate; acetic acid; potassium bromide; potassium hydroxide; sodium hydroxide; In ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1007/s12272-011-0301-2

Reference yield:

ethyl 1-(3,4-dimethoxybenzyl)-3-(1H-indol-3-yl)-1H-pyrazole-5-carboxylate (1311157-84-2) → 3-[1-(carboxymethyl)-1H-indol-3-yl]-1-(3, 4-dimethoxybenzyl)-1H-pyrazole-5-carboxylic acid (1311158-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 10 °C

1.2: 20 °C

2.1: sodium hydroxide / ethanol; water / Reflux

2.2: pH 3

With sodium hydride; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1007/s12272-011-0301-2

upstream raw materials:

3-acetylindole

ethyl 1-(3,4-dimethoxybenzyl)-3-(1H-indol-3-yl)-1H-pyrazole-5-carboxylate

C₁₄H₁₃N₃O₂

ethyl 1-(3,4-dimethoxybenzyl)-3-[1-(2-ethoxy-2-oxoethyl)-1H-indol-3-yl]-1H-pyrazole-5-carboxylate

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