ETHYL 4-BROMO-5-METHOXY-1H-INDOLE-2-CARBOXYLATE

Base Information

• Chemical Name: ETHYL 4-BROMO-5-METHOXY-1H-INDOLE-2-CARBOXYLATE
• CAS No.: 30933-69-8
• Molecular Formula: C₁₂H₁₂BrNO₃
• Molecular Weight: 298.136
• Hs Code.: 2933990090
• Mol file: 30933-69-8.mol

Synonyms:3-ISOXAZOLECARBOXYLIC ACID,4-BENZOYL-,ETHYL ESTER;4-bromo-5-methoxy-indole-2-carboxylic acid ethyl ester;3-Brom-2-ethoxycarbonyl-5-methoxyindol;Ethyl-4-bromo-5-methoxyindole-2-carboxylate;ethyl-4-benzoylisoxazole-3-carboxylate;3-Carbethoxy-4-benzoyl-isoxazol;4-Benzoyl.isoxazol-3-carbonsaeure-ethylester;4-Benzoyl-3-isoxazolecarboxylic acid ethyl ester;Bromo-4-methoxy-5-ethoxycarbonyl-2-indol;4-benzoyl-isoxazole-3-carboxylic acid ethyl ester;

Chemical Property of ETHYL 4-BROMO-5-METHOXY-1H-INDOLE-2-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 424.188oC at 760 mmHg
• Flash Point: 210.342oC
• PSA: 51.32000
• Density: 1.518g/cm3
• LogP: 3.11570

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl4-bromo-5-methoxy-1h-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ETHYL 4-BROMO-5-METHOXY-1H-INDOLE-2-CARBOXYLATE

There total 7 articles about ETHYL 4-BROMO-5-METHOXY-1H-INDOLE-2-CARBOXYLATE 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: 87.0%

ethyl 4,6-dibromo-5-methoxy-1H-indole-2-carboxylate → 6-bromo-5-methoxy-1H-indole-2-carboxylic acid ethyl ester (128593-40-8) + ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylate (30933-69-8)

Guidance literature:

With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jo035819k

Reference yield: 78.0%

ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9) → ethyl 3,4-dibromo-5-methoxy-1H-indole-2-carboxylate (30933-70-1) + ethyl 3-bromo-5-methoxy-1H-indole-2-carboxylate (92622-96-3) + ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylate (30933-69-8) + ethyl 3,6-dibromo-5-methoxyindole-2-carboxylate

Guidance literature:

With bromine; In acetic acid; for 1h; Product distribution; Mechanism; Ambient temperature; other methoxy derivatives of ethyl indole-2-acrboxylate; pyridinium bromide perbromide or N-bromosuccinimide (NBS) as bromination agent; var. solvents, temperatures and reaction times;

Reference yield: 71.3%

ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9) → ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylate (30933-69-8)

Guidance literature:

With bromine; In acetic acid; for 24h; Ambient temperature;

DOI:10.1021/jo00199a004

upstream raw materials:

ethyl 5-methoxy-1H-indole-2-carboxylate

2-[(3-Bromo-4-methoxy-phenyl)-hydrazono]-propionic acid ethyl ester

ethyl 3-bromo-5-methoxy-1H-indole-2-carboxylate

Downstream raw materials:

2-(9-chloro-7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

ethyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

2-(7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

5-methoxyindole-4-carboxaldehyde

Refernces

• 1、 Chae, Junghyun,Buchwald, Stephen L.. "Palladium-Catalyzed Regioselective Hydrodebromination of Dibromoindoles: Application to the Enantioselective Synthesis of Indolodioxane U86192A". . p. 3336 - 3339. Retrieved 2007/10/03.
• 2、 Hino,Hasegawa,Liu,Nakagawa. "2-Hydroxy-1-substituted-1,2,3,4-tetrahydro-β-carbolines. The Pictet-Spengler reaction of N-Hy-droxytryptamine with aldehydes". . p. 59 - 64. Retrieved 2007/10/02.