Benzyl 5-Methoxy-2-Methylindole-3-acetate

Base Information

• Chemical Name: Benzyl 5-Methoxy-2-Methylindole-3-acetate
• CAS No.: 3285-40-3
• Molecular Formula: C19H19NO3
• Molecular Weight: 309.365
• Hs Code.: 2933990090
• Mol file: 3285-40-3.mol

Synonyms:Benzyl 5-Methoxy-2-methylindole-3-acetate;

Chemical Property of Benzyl 5-Methoxy-2-Methylindole-3-acetate

Chemical Property:

• Boiling Point: 490.5±40.0 °C(Predicted)
• PKA: 16.92±0.30(Predicted)
• PSA: 51.32000
• Density: 1.210±0.06 g/cm3(Predicted)
• LogP: 3.77080

Purity/Quality:

95% ^*data from raw suppliers

Benzyl 5-Methoxy-2-methylindole-3-acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Benzyl 5-Methoxy-2-methylindole-3-acetate is used in the synthesis of indomethacin analogues as nonsteroidal anti-inflammatory agents, that inhibit P-glycoprotein and/or MDR protein without COX-1/COX-2 inhibitory activity. As well used to synthesize indole-based prostaglandin D receptor antagonists.

Technology Process of Benzyl 5-Methoxy-2-Methylindole-3-acetate

There total 5 articles about Benzyl 5-Methoxy-2-Methylindole-3-acetate 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%

5-Methoxy-2-methylindole-3-acetic acid (2882-15-7) + benzyl chloroformate (501-53-1,94274-21-2) → (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid benzyl ester (3285-40-3)

Guidance literature:

With 4-dimethylaminopyridine; 2-amino-3,3-dimethylbutane; In dichloromethane; at 0 ℃; for 0.583333h;

DOI:10.1016/j.bmcl.2010.07.132

Reference yield: 84.0%

5-Methoxy-2-methylindole-3-acetic acid (2882-15-7) + benzyl alcohol (100-51-6,185532-71-2) → (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid benzyl ester (3285-40-3)

Guidance literature:

5-Methoxy-2-methylindole-3-acetic acid; With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; for 0.166667h; Inert atmosphere;

benzyl alcohol; In dichloromethane; for 12h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.05.063

Reference yield: 67.0%

5-methoxy-2-methyl-1H-indole (1076-74-0) + benzyl iodoacetate (81867-37-0) → (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid benzyl ester (3285-40-3)

Guidance literature:

5-methoxy-2-methyl-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃;

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; for 0.5h;

benzyl iodoacetate; In tetrahydrofuran; diethyl ether; hexane; at 20 ℃; for 17h;

DOI:10.1002/ejoc.200900520

upstream raw materials:

methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate

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

benzyl iodoacetate

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

Downstream raw materials:

2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester

[1-(2-chloropyridine-4-carbonyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid benzyl ester

benzyl [5-methoxy-2-methyl-1-(4-{[(2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl]methoxy}benzoyl)-1H-indol-3-yl]acetate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid