1H-Indole-3-acetonitrile, 5-methoxy-2-methyl-

Base Information

• Chemical Name: 1H-Indole-3-acetonitrile, 5-methoxy-2-methyl-
• CAS No.: 15992-11-7
• Molecular Formula: C12H12N2O
• Molecular Weight: 200.24
• Mol file: 15992-11-7.mol

Synonyms:5-methoxy-2-methyl-1H-indole-3-acetonitrile;(5-methoxy-2-methyl-indol-3-yl)-acetonitrile;(5-Methoxy-2-methyl-3-indolyl)acetonitril;5-Methoxy-3-indolyl-propionitril;5-Methoxy-2-methyl-3-cyanomethylindole;

Chemical Property of 1H-Indole-3-acetonitrile, 5-methoxy-2-methyl-

Chemical Property:

• PSA: 48.81000
• LogP: 2.55098

Purity/Quality:

95%-98% ^*data from raw suppliers

2-(5-Methoxy-2-methyl-1H-indol-3-yl)acetonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-3-acetonitrile, 5-methoxy-2-methyl-

There total 10 articles about 1H-Indole-3-acetonitrile, 5-methoxy-2-methyl- 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: 97.0%

1-Acetyl-2-methyl-5-methoxy-3-oxoindoline (71653-67-3) → (5-methoxy-2-methyl-1H-indol-3-yl)-acetonitrile (15992-11-7)

Guidance literature:

With potassium hydroxide; In methanol; for 3h; Ambient temperature;

DOI:10.1055/s-1982-30062

Reference yield: 51.0%

5-methoxy-2-methyl-1H-indole (1076-74-0) + cyanomethyl bromide (590-17-0) → (5-methoxy-2-methyl-1H-indol-3-yl)-acetonitrile (15992-11-7)

Guidance literature:

5-methoxy-2-methyl-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;

With zinc(II) chloride; In tetrahydrofuran; hexane; at 0 - 2 ℃; for 2h;

cyanomethyl bromide; In tetrahydrofuran; hexane; at 20 ℃; for 24h;

Reference yield: 44.0%

5-methoxy-2-methyl-1H-indole (1076-74-0) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + trimethylsilyl cyanide (7677-24-9) → (5-methoxy-2-methyl-1H-indol-3-yl)-acetonitrile (15992-11-7)

Guidance literature:

5-methoxy-2-methyl-1H-indole; formaldehyd; With acetic acid; dimethyl amine; In water; at 0 - 20 ℃; for 2h;

With 3-(Dimethylaminomethyl)indole; methyl iodide; In dichloromethane; toluene; at 20 ℃; for 12h; Inert atmosphere;

trimethylsilyl cyanide; With tetrabutyl ammonium fluoride; In dichloromethane; toluene; at 20 ℃; for 4h; Inert atmosphere;

upstream raw materials:

diethyl 1-cyanomethylphosphonate

1-Acetyl-2-methyl-5-methoxy-3-oxoindoline

1-Acetyl-3-cyanomethyl-5-methoxy-2-methylindole

5-methoxy-2-methyl-1H-indole

Downstream raw materials:

3-(cyanomethyl)-2-methyl-1-(phenylmethyl)-5-methoxyindole

5-Methoxy-2-methylindole-3-acetic acid

Refernces

• 1、 Labrière, Christophe,Talapatra, Sandeep K.,Thoret, Sylviane,Bougeret, Cécile,Kozielski, Frank,Guillou, Catherine. "New MKLP-2 inhibitors in the paprotrain series: Design, synthesis and biological evaluations". supporting information. p. 721 - 734. Retrieved 2016/02/09.
• 2、 Dillard, Robert D.,Bach, Nicholas J.,Draheim, Susan E.,Berry, Dennis R.,Carlson, Donald G.,Chirgadze, Nickolay Y.,Clawson, David K.,Hartley, Lawrence W.,Johnson, Lea M.,Jones, Noel D.,McKinney, Emma R.,Mihelich, Edward D.,Olkowski, Jennifer L.,Schevitz, Richard W.,Smith, Amy C.,Snyder, David W.,Sommers, Cynthia D.,Wery, Jean-Pierre. "Indole inhibitors of human nonpancreatic secretory phospholipase A2. 1. Indole-3-acetamides". . p. 5119 - 5136. Retrieved 2007/10/03.