1H-Indole, 3-(2-azidoethyl)-6,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-

Base Information

• Chemical Name: 1H-Indole, 3-(2-azidoethyl)-6,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-
• CAS No.: 153718-70-8
• Molecular Formula: C19H20N4O4S
• Molecular Weight: 400.458
• DSSTox Substance ID: DTXSID30456410
• Nikkaji Number: J1.139.153B
• Wikidata: Q82278865
• Mol file: 153718-70-8.mol

Synonyms:153718-70-8;1H-Indole, 3-(2-azidoethyl)-6,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-;DTXSID30456410;1-Tosyl-3-(2-azidoethyl)-6,7-dimethoxy-1H-indole

Chemical Property of 1H-Indole, 3-(2-azidoethyl)-6,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 400.12052631
• Heavy Atom Count: 28
• Complexity: 668

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=C(C3=C2C(=C(C=C3)OC)OC)CCN=[N+]=[N-]

Technology Process of 1H-Indole, 3-(2-azidoethyl)-6,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]-

There total 11 articles about 1H-Indole, 3-(2-azidoethyl)-6,7-dimethoxy-1-[(4-methylphenyl)sulfonyl]- 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: 89.0%

p-toluenesulfonyl chloride (98-59-9) + 3-(2-Azidoethyl)-6,7-dimethoxyindole (203307-89-5) → 3-(2-Azidoethyl)-6,7-dimethoxy-1-<(4-methylphenyl)sulfonyl>indole (153718-70-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; 1.) 0 deg C, 1 h, 2.) r.t., overnight;

DOI:10.1055/s-1999-3462

Reference yield: 82.0%

Toluene-4-sulfonic acid 2-[6,7-dimethoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester (153718-68-4) → 3-(2-Azidoethyl)-6,7-dimethoxy-1-<(4-methylphenyl)sulfonyl>indole (153718-70-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 0.75h;

DOI:10.1021/ja00084a026

Reference yield:

2-nitroveratraldehyde (55149-84-3) → 3-(2-Azidoethyl)-6,7-dimethoxy-1-<(4-methylphenyl)sulfonyl>indole (153718-70-8)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium hydroxide / ethanol; N,N-dimethyl-formamide / 1.25 h / -2 °C

2: palladium on carbon; formic acid; ammonium formate / methanol / 1 h

3: 2 h / 0 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / Reflux

5: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / toluene / 9 h

6: potassium tert-butylate / tetrahydrofuran / 6 h / 0 °C

With lithium aluminium tetrahydride; formic acid; diphenyl phosphoryl azide; palladium on carbon; potassium tert-butylate; ammonium formate; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 5: Mitsunobu reaction;

DOI:10.1039/c1ob05058c

upstream raw materials:

Toluene-4-sulfonic acid 2-[6,7-dimethoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl ester

p-toluenesulfonyl chloride

3-(2-Azidoethyl)-6,7-dimethoxyindole

6,7-dimethoxy-1H-indole

Downstream raw materials:

5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one

5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-(tert-butyldimethylsilyloxymethyl)-10-spiro-4'-(2'-bromo)-cyclohexa-2',5'-dien-1'-one

(+)-5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-triazaacephenanthrylen-6-one-8-(hydroxymethyl)-10-spiro-4'-(2'-bromo)cyclohexa-2',5'-dien-1'-one

(+)-5-(toluene-4-sulfonyl)-3,5,7,8,9,10-hexahydro-2H-1,5,7-triazaacephenanthrylen-6-one-8-methoxy-10-spiro-4'-(2'-bromo)cyclohexa-2',5'-dien-1'-one