2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole

Base Information

• Chemical Name: 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole
• CAS No.: 1276539-11-7
• Molecular Formula: C₂₇H₃₂N₂O₄S
• Molecular Weight: 480.628
• Mol file: 1276539-11-7.mol

Synonyms:2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole

Chemical Property of 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole

There total 2 articles about 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole 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:

di-tert-butyl dicarbonate (24424-99-5) + C22H24N2O2S → 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole (1276539-11-7)

Guidance literature:

With triethylamine; In methanol; for 5h; Reflux;

DOI:10.1021/ol200437k

Reference yield:

3-(2-hydroxyethyl)-1-(benzenesulfonyl)indole (99655-69-3) → 2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole (1276539-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 - -50 °C

1.2: 4 h / -50 - 20 °C

1.3: -78 - 20 °C

2.1: dmap; triethylamine / dichloromethane / 20 °C

3.1: potassium carbonate; lithium iodide / acetonitrile / 48 h / 85 °C

4.1: triethylamine / methanol / 5 h / Reflux

With dmap; potassium carbonate; triethylamine; lithium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ol200437k

Reference yield: 75.0%

2-allyl-3-[2-(N-allyl-N-tert-butoxycarbonylamino)ethyl]-1-(phenylsulfonyl)indole (1276539-11-7) → 3-(tert-butoxycarbonyl)-8-(phenylsulfonyl)-2,3,4,7-tetrahydro-1H-azonino[5,4-b]indole

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2.5h; Reflux; Inert atmosphere;

DOI:10.1021/ol200437k

upstream raw materials:

di-tert-butyl dicarbonate

3-(2-hydroxyethyl)-1-(benzenesulfonyl)indole

Downstream raw materials:

C₂₅H₂₆N₂O₂S