tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate

Base Information

• Chemical Name: tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate
• CAS No.: 220034-71-9
• Molecular Formula: C₂₄H₃₀N₂O₆S
• Molecular Weight: 474.578
• Mol file: 220034-71-9.mol

Synonyms:tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate

Chemical Property of tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate

There total 14 articles about tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate 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:

4,7-dimethoxylindole (23876-39-3) → tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate (220034-71-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: POCl₃ / 1.5 h / 0 °C

2.1: ammonium acetate; acetic acid / 3 h / Heating

3.1: KOH / tetrahydrofuran / 0.08 h / 0 °C

3.2: 54 percent / tetrahydrofuran / 1 h / 20 °C

4.1: LiAlH₄ / diethyl ether; CH₂Cl₂ / 0.25 h / 0 °C

5.1: sodium hydride / tetrahydrofuran / 0.08 h / 20 °C

5.2: 200 mg / tetrahydrofuran / 1 h / 20 °C

With ammonium acetate; potassium hydroxide; lithium aluminium tetrahydride; sodium hydride; acetic acid; trichlorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm051247f

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2-[4,7-dimethoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]ethylamine (1026325-96-1) → di-tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)imidodicarbonate + tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate (220034-71-9)

Guidance literature:

2-[4,7-dimethoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]ethylamine; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jm051247f

Reference yield:

N,N-dibenzyl-2-(4,7-dimethoxy-indol-3-yl)-2-oxo-acetamide (96005-26-4) → tert-butyl (2-{4,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)carbamate (220034-71-9)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / diethyl ether

2: NaH / tetrahydrofuran

3: H₂ / Pd(OH)2 / ethanol

4: CH₂Cl₂

With lithium aluminium tetrahydride; hydrogen; sodium hydride; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo9815397

upstream raw materials:

di-tert-butyl dicarbonate

2-[4,7-dimethoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]ethylamine

4,7-dimethoxy-3-(2-nitro-vinyl)-1H-indole

4,7-dimethoxylindole

Downstream raw materials:

tert-butyl (2-{1-(3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-7-[(4-methylphenyl)sulfonyl]-4,8-dioxo-1,4,7,8-tetrahydro-pyrrolo[3,2-f]indazol-5-yl}ethyl)carbamate

tert-butyl (2-{1-(3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-5-[(4-methylphenyl)sulfonyl]-4,8-dioxo-1,4,5,8-tetrahydro-pyrrolo[2,3-f]indazol-7-yl}ethyl)carbamate

7-(3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-5-(toluene-4-sulfonyl)-2,3,5,9-tetrahydro-1,5,8,9-tetraaza-cyclopenta[e]acenaphthylen-6-one

9-(3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-5-[(4-methylphenyl)sulfonyl]-2,3,5,7-tetrahydro-6H-pyrazolo[3,4-h]pyrrolo[4,3,2-de]quinolin-6-one

Refernces

• 1、 Aubart, Kelly Marshall,Heathcock, Clayton H.. "A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D". . p. 16 - 22. Retrieved 2007/10/03.