N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

Base Information

Chemical Name:N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide
CAS No.:126502-30-5
Molecular Formula:C₃₁H₃₂BrN₃O₅S
Molecular Weight:638.582
Hs Code.:

Synonyms:N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

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Chemical Property of N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

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Technology Process of N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

There total 7 articles about N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide 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: 67.0%

: 92748-09-9
2-bromobenzene-1-sulfonamide

: 107786-57-2
4-{[5-(2-cyclopentylacetamido)-1-methyl-1H-indol-3-yl]methyl}-3-methoxybenzoic acid

: 126502-30-5
N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;
DOI:10.1021/jm00168a037

Reference yield:

: 70264-94-7
methyl 4-(bromomethyl)-3-methoxybenzoate

: 126502-30-5
N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 45 percent / silver(I) oxide / dioxane / 20 h / 60 °C

2: 1.) NaH / 1.) THF, 10 min, 2.) 30 min

3: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr

4: 1.) 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2.) LiOH monohydrate / 1.) CH₂Cl₂, 18 h, 2.) THF, MeOH, water, 20 h

5: 67 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

With dmap; lithium hydroxide; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jm00168a037

Reference yield:

: 107786-36-7
4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester

: 126502-30-5
N-{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indol-5-yl}-2-cyclopentyl-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, 10 min, 2.) 30 min

2: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr

3: 1.) 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2.) LiOH monohydrate / 1.) CH₂Cl₂, 18 h, 2.) THF, MeOH, water, 20 h

4: 67 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

With dmap; lithium hydroxide; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm00168a037