{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester

Base Information

• Chemical Name: {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester
• CAS No.: 126502-34-9
• Molecular Formula: C₂₉H₂₉BrN₄O₆S
• Molecular Weight: 641.542
• Mol file: 126502-34-9.mol

Synonyms:{3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester

Chemical Property of {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester

There total 12 articles about {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester 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: 93.0%

2-bromobenzene-1-sulfonamide (92748-09-9) + 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid (107786-94-7) → {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester (126502-34-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 18h;

DOI:10.1021/jm00168a037

Reference yield:

methyl 4-(bromomethyl)-3-methoxybenzoate (70264-94-7) → {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester (126502-34-9)

Guidance literature:

Multi-step reaction with 10 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: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h

5: 98 percent / Rose Bengal, O₂ / methanol / 1.5 h / Irradiation

6: 59 percent / NH₂OH*HCl, pyridine / 18 h / Heating

7: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h

8: 96 percent / 170 °C

9: 98 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h

10: 93 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

With 4-methyl-morpholine; pyridine; dmap; lithium hydroxide; hydroxylamine hydrochloride; hydrogen; oxygen; rose bengal; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/jm00168a037

Reference yield:

4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (107786-36-7) → {3-[4-(2-Bromo-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-1-methyl-1H-indazol-5-yl}-carbamic acid cyclopentyl ester (126502-34-9)

Guidance literature:

Multi-step reaction with 9 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: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h

4: 98 percent / Rose Bengal, O₂ / methanol / 1.5 h / Irradiation

5: 59 percent / NH₂OH*HCl, pyridine / 18 h / Heating

6: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h

7: 96 percent / 170 °C

8: 98 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h

9: 93 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

With 4-methyl-morpholine; pyridine; dmap; lithium hydroxide; hydroxylamine hydrochloride; hydrogen; oxygen; rose bengal; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jm00168a037

upstream raw materials:

2-bromobenzene-1-sulfonamide

4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid

cyclopentyl chloroformate

methyl 4-(bromomethyl)-3-methoxybenzoate