3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol

Base Information

• Chemical Name: 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol
• CAS No.: 192773-95-8
• Molecular Formula: C₃₅H₃₈N₂O₂
• Molecular Weight: 518.699

Synonyms:3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol

Chemical Property of 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol

There total 15 articles about 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol 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-(N,N-dimethylamino)ethanol (108-01-0) + 4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide (192773-94-7) → 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol (192773-95-8)

Guidance literature:

With borane; In tetrahydrofuran; methanol;

Reference yield:

5-benzyloxytryptamine (20776-45-8) → 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol (192773-95-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrahydrofuran / Heating

2.1: pyridine hydrobromide perbromide / tetrahydrofuran; CHCl₃

3.1: Na₂CO₃; LiCl; Pd(PPh₃)4 / toluene; ethanol / 1.25 h / Heating

4.1: aq. hydrazine / tetrahydrofuran; ethanol

5.1: HOBT; EDAC / dimethylformamide; CH₂Cl₂

6.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

6.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / 3 h / Heating

7.1: H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 760 Torr

8.1: aq. hydrazine / tetrahydrofuran; ethanol

9.1: 91 percent / HOBT; EDAC / CH₂Cl₂

10.1: BH₃*THF / tetrahydrofuran / Heating

10.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; hydrogen; pyridinium hydrobromide perbromide; sodium carbonate; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; toluene; 3.1: modified Suzuki reaction;

DOI:10.1016/S0960-894X(00)00708-3

Reference yield:

N-[2-(5-benzyloxy-indol-3-yl)-ethyl]-phthalimide (53157-45-2) → 3-[2-[4-(4-benzyloxyphenyl)butylamino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-ol (192773-95-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine hydrobromide perbromide / tetrahydrofuran; CHCl₃

2.1: Na₂CO₃; LiCl; Pd(PPh₃)4 / toluene; ethanol / 1.25 h / Heating

3.1: aq. hydrazine / tetrahydrofuran; ethanol

4.1: HOBT; EDAC / dimethylformamide; CH₂Cl₂

5.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

5.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / 3 h / Heating

6.1: H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 760 Torr

7.1: aq. hydrazine / tetrahydrofuran; ethanol

8.1: 91 percent / HOBT; EDAC / CH₂Cl₂

9.1: BH₃*THF / tetrahydrofuran / Heating

9.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; hydrogen; pyridinium hydrobromide perbromide; sodium carbonate; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: modified Suzuki reaction;

DOI:10.1016/S0960-894X(00)00708-3

upstream raw materials:

4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide

4-(4-hydroxyphenyl)butanoic acid

5-benzyloxytryptamine

4-(4-benzyloxyphenyl)butyric acid

Downstream raw materials:

[4-(4-benzyloxyphenyl)-butyl]-[2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]carbamic acid benzyl ester

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