4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

Base Information

Chemical Name:4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid
CAS No.:145889-44-7
Molecular Formula:C₂₇H₃₄N₂O₄
Molecular Weight:450.578
Hs Code.:

Synonyms:4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

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Chemical Property of 4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

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Technology Process of 4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

There total 7 articles about 4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic 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:

: 1670-81-1,142396-03-0
1H-Indole-5-carboxylic acid

: 145889-44-7
4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 24 h / Ambient temperature

2: 32 percent / dimethylformamide / 24 h / 80 °C

3: 1.) NaH / 1.) DNF, 0 deg C, 1 h, 2.) DMF, from 0 deg C to RT, 1 h

4: H₂ / 10percent Pd/C / tetrahydrofuran; methanol / 1.5 h

5: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 36 h / Ambient temperature

6: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature

With dmap; lithium hydroxide; hydrogen; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00055a011

Reference yield:

: 136564-69-7
1H-indole-5-carboxylic acid benzyl ester

: 145889-44-7
4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 32 percent / dimethylformamide / 24 h / 80 °C

2: 1.) NaH / 1.) DNF, 0 deg C, 1 h, 2.) DMF, from 0 deg C to RT, 1 h

3: H₂ / 10percent Pd/C / tetrahydrofuran; methanol / 1.5 h

4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 36 h / Ambient temperature

5: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature

With dmap; lithium hydroxide; hydrogen; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00055a011

Reference yield:

: 136564-71-1
methyl 4-<<5-(benzyloxycarbonyl)indol-3-yl>methyl>-3-methoxybenzoate

: 145889-44-7
4-[5-(2-Ethyl-butylcarbamoyl)-1-propyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DNF, 0 deg C, 1 h, 2.) DMF, from 0 deg C to RT, 1 h

2: H₂ / 10percent Pd/C / tetrahydrofuran; methanol / 1.5 h

3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 36 h / Ambient temperature

4: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature

With dmap; lithium hydroxide; hydrogen; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm00055a011