2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester

Base Information

• Chemical Name: 2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester
• CAS No.: 442549-49-7
• Molecular Formula: C₁₃H₁₄BrNO₅
• Molecular Weight: 344.162
• Mol file: 442549-49-7.mol

Synonyms:

Chemical Property of 2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester

There total 1 articles about 2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl 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: 93.0%

2-bromo-4-methoxyaniline (32338-02-6) + dimethyl acetylenedicarboxylate (762-42-5) → 2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester (442549-49-7)

Guidance literature:

In methanol; for 8h; Heating;

DOI:10.1016/j.bmc.2006.10.037

Reference yield:

2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester (442549-49-7) → 8-[Ethyl-(1-ethyl-pyrrolidin-3-yl)-amino]-6-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / diphenyl ether; various solvent(s) / 0.75 h / 240 - 245 °C

2: 97 percent / lithium hydroxide monohydrate / tetrahydrofuran; methanol; H₂O / 5 h / 20 °C

3: 58 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; ethyldiisopropylamine / dimethylformamide / 16 h / 20 °C

4: 80 percent / NaH / 1-methyl-pyrrolidin-2-one / 4.5 h / 20 °C

5: molecular sieves 4 Angstroem; rac-BINAP; Cs₂CO₃ / Pd₂(dba)3 / toluene / 17 h / Heating

6: 0.163 g / aq. HCl / methanol / 0.75 h / 20 °C

With hydrogenchloride; lithium hydroxide; 4 A molecular sieve; sodium hydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diphenylether; water; N,N-dimethyl-formamide; toluene; 5: Buchwald-Hartwig coupling;

DOI:10.1016/j.bmc.2006.10.037

Reference yield:

2-(2-bromo-4-methoxyphenylamino)but-2-enedioic acid dimethyl ester (442549-49-7) → 8-[(2-dimethylamino-ethyl)-methyl-amino]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide (919794-65-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / diphenyl ether; various solvent(s) / 0.75 h / 240 - 245 °C

2: 97 percent / lithium hydroxide monohydrate / tetrahydrofuran; methanol; H₂O / 5 h / 20 °C

3: 58 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium BF₄; 1-hydroxybenzotriazole; ethyldiisopropylamine / dimethylformamide / 16 h / 20 °C

4: 80 percent / NaH / 1-methyl-pyrrolidin-2-one / 4.5 h / 20 °C

5: molecular sieves 4 Angstroem; rac-BINAP; Cs₂CO₃ / Pd₂(dba)3 / toluene / 17 h / Heating

With lithium hydroxide; 4 A molecular sieve; sodium hydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diphenylether; water; N,N-dimethyl-formamide; toluene; 5: Buchwald-Hartwig coupling;

DOI:10.1016/j.bmc.2006.10.037

upstream raw materials:

2-bromo-4-methoxyaniline

dimethyl acetylenedicarboxylate

Downstream raw materials:

8-bromo-4-chloro-6-methoxy-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

8-bromo-6-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

8-bromo-4-methylamino-6-methoxyquinoline-2-carboxylic acid [4-(morpholin-4-yl)phenyl]amide

8-bromo-4-dimethylamino-6-methoxy-quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide