Diethyl 3-isopropyl-1H-pyrrole-2,4-dicarboxylate

Base Information

• Chemical Name: Diethyl 3-isopropyl-1H-pyrrole-2,4-dicarboxylate
• CAS No.: 651744-38-6
• Molecular Formula: C13H19NO4
• Molecular Weight: 253.29426
• Mol file: 651744-38-6.mol

Synonyms:DIETHYL 3-ISOPROPYL-1H-PYRROLE-2,4-DICARBOXYLATE

Chemical Property of Diethyl 3-isopropyl-1H-pyrrole-2,4-dicarboxylate

Chemical Property:

• Boiling Point: 397.144 °C at 760 mmHg
• PKA: 13.83±0.50(Predicted)
• Flash Point: 193.986 °C
• PSA: 68.39000
• Density: 1.118 g/cm³
• LogP: 2.49150

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl3-isopropyl-1H-pyrrole-2,4-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Diethyl 3-isopropyl-1H-pyrrole-2,4-dicarboxylate

There total 2 articles about Diethyl 3-isopropyl-1H-pyrrole-2,4-dicarboxylate 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: 60.0%

Ethyl isocyanoacetate (2999-46-4) + isobutyraldehyde (78-84-2) → diethyl 3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate (651744-38-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 19h;

Reference yield: 30.0%

ethyl 2-isocyanoacetate + isobutyraldehyde (78-84-2) → diethyl 3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate (651744-38-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 50 ℃;

Reference yield:

diethyl 3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate (651744-38-6) → 4-[3-[(methoxyamino)carbonyl]phenoxy]-5-(1-methylethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: NaH; O-(diphenylphosphinyl)hydroxylamine / dimethylformamide / 2 h

2: 90 percent / 6 h / 165 °C

3: POCl₃; Et₃N / toluene / 6 h / Heating

4: 18 mg / K₂CO₃ / dimethylformamide / 18 h / 25 °C

With O-(diphenylphosphinyl)hydroxylamine; sodium hydride; potassium carbonate; triethylamine; trichlorophosphate; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0501275

upstream raw materials:

Ethyl isocyanoacetate

isobutyraldehyde

Downstream raw materials:

diethyl 1-amino-3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate

ethyl 4-chloro-5-iso-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

ethyl 5-isopropyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

5-isopropyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carbonitrile

Refernces

• 1、 Fink, Brian E.,Vite, Gregory D.,Mastalerz, Harold,Kadow, John F.,Kim, Soong-Hoon,Leavitt, Kenneth J.,Du, Karen,Crews, Donald,Mitt, Toomas,Wong, Tai W.,Hunt, John T.,Vyas, Dolatrai M.,Tokarski, John S.. "New dual inhibitors of EGFR and HER2 protein tyrosine kinases". . p. 4774 - 4779. Retrieved 2007/10/03.