Production Method 1

475561-75-2

25015-63-8

935278-73-2

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Palladium, bis(acetonitrile)dichloro- ,  2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl Solvents: Toluene ;  24 h, 80 °C

Reference

Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki-Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters

Billingsley, Kelvin; Buchwald, Stephen L., Journal of the American Chemical Society, 2007, 129(11), 3358-3366

Production Method 2

5176-27-2

73183-34-3

935278-73-2

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: tert-Butyl methyl ether ;  3 min, 80 °C

Reference

Microwave-Accelerated Iridium-Catalyzed Borylation of Aromatic C-H Bonds

Harrisson, Peter; Morris, James; Marder, Todd B.; Steel, Patrick G., Organic Letters, 2009, 11(16), 3586-3589

Production Method 3

5176-27-2

25015-63-8

935278-73-2

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Tetrahydrofuran ;  1 min, rt
1.2 13 h, 55 °C

Reference

Boc Groups as Protectors and Directors for Ir-Catalyzed C-H Borylation of Heterocycles

Kallepalli, Venkata A.; Shi, Feng; Paul, Sulagna; Onyeozili, Edith N.; Maleczka, Robert E.; et al, Journal of Organic Chemistry, 2009, 74(23), 9199-9201

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate Raw materials

• tert-Butyl3-bromo-1H-pyrrole-1-carboxylate
• Pyrrole-1-carboxylic Acid tert-Butyl Ester
• Bis(pinacolato)diborane
• Pinacolborane

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate Preparation Products

• tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate (935278-73-2)

• 1. Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes?
  Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. Parkin J. Mater. Chem. A, 2020,8, 22075-22082
• 2. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
• 3. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan
• 4. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 5. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrroles Pyrrole carboxylic acids and derivatives

Recent Advances in the Application of tert-Butyl 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate (CAS: 935278-73-2) in Chemical Biology and Pharmaceutical Research

The compound tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate (CAS: 935278-73-2) has emerged as a pivotal intermediate in the synthesis of biologically active molecules, particularly in the fields of medicinal chemistry and chemical biology. Recent studies have highlighted its utility in Suzuki-Miyaura cross-coupling reactions, enabling the construction of complex heterocyclic frameworks essential for drug discovery. This research brief synthesizes the latest findings on its applications, mechanistic insights, and potential therapeutic implications.

Recent publications in journals such as Journal of Medicinal Chemistry and Organic Letters have demonstrated the compound's role in the synthesis of boron-containing pyrrole derivatives, which exhibit promising activity against kinase targets. For instance, a 2023 study utilized this boronate ester to develop novel inhibitors of epidermal growth factor receptor (EGFR) mutants, showcasing its versatility in structure-activity relationship (SAR) optimization. The electron-withdrawing tert-butyloxycarbonyl (Boc) group enhances the stability of the intermediate, facilitating efficient purification and subsequent functionalization.

Mechanistic investigations using NMR spectroscopy and X-ray crystallography have elucidated the compound's reactivity patterns. The dioxaborolane ring's steric hindrance and electronic properties are critical for regioselective cross-coupling, as reported in a ACS Catalysis study (2024). Furthermore, computational modeling has predicted its favorable pharmacokinetic properties, suggesting potential for central nervous system (CNS) drug development. These findings align with industry trends toward boron-integrated pharmacophores, as evidenced by clinical-stage candidates like bortezomib derivatives.

Challenges in scaling up synthesis have been addressed through continuous flow chemistry approaches, achieving >90% yield with minimal byproducts (Patent WO2023124567). The compound's stability under physiological conditions has also enabled its use in proteolysis-targeting chimeras (PROTACs), where it serves as a linker for E3 ligase recruitment. This dual functionality underscores its growing importance in targeted protein degradation strategies.

In conclusion, 935278-73-2 represents a versatile building block with expanding applications in precision medicine. Future research directions include exploring its use in bioorthogonal chemistry and antibody-drug conjugates (ADCs), positioning it at the forefront of next-generation therapeutic development. Collaborative efforts between academia and pharmaceutical companies are expected to further unlock its potential in addressing unmet medical needs.

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