2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 126260-53-5
• Molecular Formula: C₂₇H₃₂BrN₃O₆S
• Molecular Weight: 606.538
• Mol file: 126260-53-5.mol

Synonyms:

Chemical Property of 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 8 articles about 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl 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: 63.0%

N-tert-butoxycarbonyl-proline (15761-39-4,59433-50-0) + 5-bromo-7-(p-toluenesulfonyloxy)tryptamine (201684-57-3) → 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (126260-53-5)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(97)10255-1

Reference yield:

(E)-5-bromo-3-nitrovinyl-7-(p-toluenesulfonyloxy)indole (126260-59-1) → 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (126260-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / LIAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

2: 63 percent / Et₃N, diethyl phosphorocyanidate / dimethylformamide / 0.5 h / Ambient temperature

With lithium aluminium tetrahydride; diethyl cyanophosphonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10255-1

Reference yield:

ethyl 5-bromo-7-tosyloxyindole-2-carboxylate (126260-58-0) → 2-{2-[5-Bromo-7-(toluene-4-sulfonyloxy)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (126260-53-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / conc. H₂SO₄ / acetic acid; H₂O / 10 h / 130 °C

2: 74 percent / copper-chromite, quinoline / 2.5 h / 200 °C

3: 1) POCl₃, 2) NaHCO₃ / 1) room temperature, 3 h, 2) H₂O, 80 deg C, 30 min

4: 100 percent / AcONH₄ / 3 h / Heating

5: 72 percent / LIAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

6: 63 percent / Et₃N, diethyl phosphorocyanidate / dimethylformamide / 0.5 h / Ambient temperature

With quinoline; lithium aluminium tetrahydride; copper chromite; diethyl cyanophosphonate; sulfuric acid; ammonium acetate; sodium hydrogencarbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10255-1

upstream raw materials:

(E)-5-bromo-3-nitrovinyl-7-(p-toluenesulfonyloxy)indole

N^α-(tert-butyloxycarbonyl)-L-proline

ethyl 5-bromo-7-tosyloxyindole-2-carboxylate

N-tert-butoxycarbonyl-proline

Downstream raw materials:

6-Bromo-1-(4,5-dihydro-3H-pyrrol-2-yl)-9H-β-carbolin-8-ol

Toluene-4-sulfonic acid 6-bromo-1-(4,5-dihydro-3H-pyrrol-2-yl)-9H-β-carbolin-8-yl ester

Toluene-4-sulfonic acid 6-bromo-1-(4,5-dihydro-3H-pyrrol-2-yl)-4,9-dihydro-3H-β-carbolin-8-yl ester