1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid,

Base Information

• Chemical Name: 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid,
• CAS No.: 942070-38-4
• Molecular Formula: C17H26BNO6
• Molecular Weight: 351.208
• Hs Code.: 2934999090
• Mol file: 942070-38-4.mol

Synonyms:methyl N-Boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-2-carboxylate;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;1-tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate;1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)pyrrole-4-boronic acid pinacol ester;1-BOC-2-(METHOXYCARBONYL)PYRROLE-4-BORONIC ACID,PINACOL ESTER;

Chemical Property of 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid,

Chemical Property:

• Melting Point: 133-135 °C
• Boiling Point: 451.4±55.0 °C(Predicted)
• PKA: -10.33±0.70(Predicted)
• PSA: 75.99000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 2.35710
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

1-BOC-2-(methoxycarbonyl)pyrrole-4-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid,

There total 6 articles about 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid, 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: 79.0%

bis(pinacol)diborane (73183-34-3) + methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate (294659-30-6) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (942070-38-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; at 80 ℃; for 0.333333h; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1021/acs.jmedchem.9b01295

Reference yield: 75.0%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate (294659-30-6) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (942070-38-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In hexane; at 20 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo901822b

Reference yield:

4-bromopyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (156237-78-4) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (942070-38-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 3h; Inert atmosphere;

upstream raw materials:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate

bis(pinacol)diborane

4-bromopyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Downstream raw materials:

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

methyl 4-(2-nitrophenyl)-1H-pyrrole-2-carboxylate

7-{5-(methoxycarbonyl)-1H-pyrrol-3-yl}-2-(3-fluorophenyl)-2H-[1,2,3]triazolo[4,5-f]quinoline-9-carboxylic acid

7-(5-carboxy-1H-pyrrol-3-yl)-2-(3-fluorophenyl)-2H-[1,2,3]triazolo[4,5-f]quinoline-9-carboxylic acid

Refernces

• 1、 -. "ERK INHIBITOR AND USE THEREOF". Paragraph 0098; 0100. . Retrieved 2021/04/16.
• 2、 -. "SUBSTITUTED 3,4-DIHYDROPYRROLO[1,2-A]PYRAZIN-1 (2H)-ONE DERIVATIVES AS KINASE INHIBITORS". Page/Page column 102. . Retrieved 2016/10/31.