1-Tert-butyl 2-methyl 5-bromo-1H-pyrrole-1,2-dicarboxylate

Base Information

• Chemical Name: 1-Tert-butyl 2-methyl 5-bromo-1H-pyrrole-1,2-dicarboxylate
• CAS No.: 924708-81-6
• Molecular Formula: C₁₁H₁₄BrNO₄
• Molecular Weight: 304.14
• DSSTox Substance ID: DTXSID70696777
• Wikidata: Q82626475
• Mol file: 924708-81-6.mol

Synonyms:924708-81-6;1-TERT-BUTYL 2-METHYL 5-BROMO-1H-PYRROLE-1,2-DICARBOXYLATE;Methyl 5-Bromo-1-Boc-1H-pyrrole-2-carboxylate;1-O-tert-butyl 2-O-methyl 5-bromopyrrole-1,2-dicarboxylate;1-(Tert-butyl) 2-methyl 5-bromo-1H-pyrrole-1,2-dicarboxylate;DTXSID70696777;O1-tert-butyl O2-methyl 5-bromanylpyrrole-1,2-dicarboxylate;AC8996;MFCD11112102;SB63252;SY251714;CS-0363710;FT-0689856;A844244;1-TERT-BUTYL2-METHYL5-BROMO-1H-PYRROLE-1,2-DICARBOXYLATE;5-bromopyrrole-1,2-dicarboxylic acid O1-tert-butyl ester O2-methyl ester;1H-Pyrrole-1,2-dicarboxylic acid,5-bromo-,1-(1,1-dimethyl ethyl)2-methyl ester;1H-Pyrrole-1,2-dicarboxylicacid,5-bromo-,1-(1,1-dimethylethyl)2-methyl ester

Chemical Property of 1-Tert-butyl 2-methyl 5-bromo-1H-pyrrole-1,2-dicarboxylate

Chemical Property:

• PSA: 57.53000
• LogP: 2.82040
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 303.01062
• Heavy Atom Count: 17
• Complexity: 313

Purity/Quality:

97% ^*data from raw suppliers

1-tert-Butyl2-methyl5-bromo-1H-pyrrole-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(=CC=C1Br)C(=O)OC

Technology Process of 1-Tert-butyl 2-methyl 5-bromo-1H-pyrrole-1,2-dicarboxylate

There total 2 articles about 1-Tert-butyl 2-methyl 5-bromo-1H-pyrrole-1,2-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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester (934-07-6) → methyl 5-bromo-1-(tert-butoxycarbonyl)-1H-pyrrole-2-carboxylate (924708-81-6)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/acs.orglett.1c01558

Reference yield: 81.0%

2,5-dibromopyrrole-1-carboxylic acid tert-butyl ester (117657-38-2) + methyl chloroformate (79-22-1) → methyl 5-bromo-1-(tert-butoxycarbonyl)-1H-pyrrole-2-carboxylate (924708-81-6)

Guidance literature:

2,5-dibromopyrrole-1-carboxylic acid tert-butyl ester; With n-butyllithium; In diethyl ether; at -78 ℃; for 0.5h; Inert atmosphere;

methyl chloroformate; In diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo402181w

Reference yield:

4-isopropoxy-3-methoxyphenylboronic acid (875654-33-4) + methyl 5-bromo-1-(tert-butoxycarbonyl)-1H-pyrrole-2-carboxylate (924708-81-6) → methyl 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate (1519002-13-1)

Guidance literature:

4-isopropoxy-3-methoxyphenylboronic acid; methyl 5-bromo-1-(tert-butoxycarbonyl)-1H-pyrrole-2-carboxylate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; for 21.5h; Inert atmosphere; Reflux;

With methanol; sodium; for 19h; Reflux;

DOI:10.1021/jo402181w

upstream raw materials:

2,5-dibromopyrrole-1-carboxylic acid tert-butyl ester

methyl chloroformate

di-tert-butyl dicarbonate

5-bromo-1H-pyrrole-2-carboxylic acid methyl ester

Downstream raw materials:

methyl 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate

C₂₁H₂₇NO₆