methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate

Base Information

• Chemical Name: methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate
• CAS No.: 142563-82-4
• Molecular Formula: C₃₀H₃₇N₃O₅
• Molecular Weight: 519.641

Synonyms:methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate

Chemical Property of methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate

Chemical Property:

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Technology Process of methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate

There total 4 articles about methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate 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:

2-bromo-N,N-dimethylpropanamide (54537-47-2) + methyl 4-<<5-indol-3-yl>methyl>-3-methoxybenzoate (110707-74-9) → methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate (142563-82-4)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, RT, 15 min;

DOI:10.1021/jm00091a010

Reference yield:

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) → methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate (142563-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h

2: 1.) Ag₂O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h

3: 1.) NaH / 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, RT, 15 min

With dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; In dichloromethane;

DOI:10.1021/jm00091a010

Reference yield:

cyclopentylmethylamine (6053-81-2) → methyl 4-<<5--1-<1-(N,N-dimethylcarbamoyl)ethyl>indol-3-yl>methyl>-3-methoxybenzoate (142563-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h

2: 1.) Ag₂O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h

3: 1.) NaH / 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, RT, 15 min

With dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; In dichloromethane;

DOI:10.1021/jm00091a010

upstream raw materials:

2-bromo-N,N-dimethylpropanamide

methyl 4-<<5-indol-3-yl>methyl>-3-methoxybenzoate

1H-Indole-5-carboxylic acid

cyclopentylmethylamine

Downstream raw materials:

4-[5-(N-cyclopentylmethylcarbamoyl)-1-[1-(N,N-dimethylcarbamoyl)ethyl]indol-3-ylmethyl]-3-methoxybenzoic acid

1-(1-Dimethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide

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