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

Base Information

Chemical Name:4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide
CAS No.:192773-94-7
Molecular Formula:C₃₅H₃₆N₂O₃
Molecular Weight:532.682
Hs Code.:

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

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

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

There total 11 articles about 4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide 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: 91.0%

: 6686-26-6
4-(4-benzyloxyphenyl)butyric acid

: 192773-93-6
3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-ol

: 192773-94-7
4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1016/S0960-894X(00)00708-3

Reference yield:

: 20776-45-8
5-benzyloxytryptamine

: 192773-94-7
4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide

Guidance literature:: Multi-step reaction with 9 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

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:

: 53157-45-2
N-[2-(5-benzyloxy-indol-3-yl)-ethyl]-phthalimide

: 192773-94-7
4-(4-benzyloxyphenyl)-N-{2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]butyramide

Guidance literature:: Multi-step reaction with 8 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

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