7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester

Base Information

• Chemical Name: 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester
• CAS No.: 1193487-42-1
• Molecular Formula: C₁₈H₁₈BrFN₂O₃
• Molecular Weight: 409.255
• Mol file: 1193487-42-1.mol

Synonyms:7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester

Chemical Property of 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester

There total 3 articles about 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester 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: 19.0%

6-methyl 5-oxo-7-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester (1193488-47-9) + 4-bromo-2-fluoroaniline (367-24-8) → 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester (1193487-42-1)

Guidance literature:

With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In toluene; at 90 ℃; for 4h;

Reference yield:

ethyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydro-8-indolizinecarboxylate (72130-68-8) → 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester (1193487-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: 48 h / 20 °C / Inert atmosphere

2.1: 12 h / 20 °C

3.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 4 h / 90 °C

With sodium hydride; caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; toluene; mineral oil;

Reference yield:

7-Hydroxy-8-(ethoxycarbonyl)-6-methyl-2,3-dihydro-1H-indolizin-5-one (116993-42-1) → 7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester (1193487-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 12 h / 20 °C

2: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 4 h / 90 °C

With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene;

upstream raw materials:

6-methyl 5-oxo-7-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid ethyl ester

4-bromo-2-fluoroaniline

7-Hydroxy-8-(ethoxycarbonyl)-6-methyl-2,3-dihydro-1H-indolizin-5-one

ethyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydro-8-indolizinecarboxylate

Downstream raw materials:

7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid

7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,3,5,1-tetrahydro-indolizine-8-carboxylic acid (2-hydroxy-ethoxy)-amide

7-(4-Bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,1-tetrahydro-indolizine-8-carboxylic acid (2-vinyloxy-ethoxy)-amide