Production Method 1

214360-77-7

953040-54-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  0 °C; 10 min, 0 °C; 0 °C → rt; 1.5 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Ligand control in enantioselective desymmetrization of bicyclic hydrazines: Rhodium(I)-catalyzed ring-opening versus hydroarylation

Panteleev, Jane; Menard, Frederic; Lautens, Mark, Advanced Synthesis & Catalysis, 2008, 350(18), 2893-2902

Production Method 2

214360-77-7

953040-54-5

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethyl sulfoxide ;  0 °C; 30 min, > 0 °C; cooled
1.2 0 °C; 30 min, > 0 °C

Reference

A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation

Cooper, Stephen P.; Booker-Milburn, Kevin I., Angewandte Chemie, 2015, 54(22), 6496-6500

Production Method 3

25015-63-8

96-54-8

953040-54-5

850567-47-4

Reaction Conditions

1.1 Catalysts: 1-(2-Borylphenyl)-2,2,6,6-tetramethylpiperidine Solvents: Chloroform ;  5 h, rt → 80 °C

Reference

Metal-free catalytic C-H bond activation and borylation of heteroarenes

Legare, Marc-Andre; Courtemanche, Marc-Andre; Rochette, Etienne; Fontaine, Frederic-Georges, Science (Washington, 2015, 349(6247), 513-516

Production Method 4

25015-63-8

96-54-8

953040-54-5

850567-47-4

Reaction Conditions

1.1 Catalysts: Borate(1-), [2-(diethylamino)phenyl]trifluoro-, hydrogen (1:1), (T-4)- ;  10 min, rt; 2 h, 80 °C

Reference

Precatalysts and process for the metal-free functionalization of sp2 carbons using the same

, United States, , ,

Production Method 5

73183-34-3

96-54-8

953040-54-5

850567-47-4

Reaction Conditions

1.1 Catalysts: 2346606-58-2 ;  18 h, 100 °C

Reference

Catalytic C-H Borylation Using Iron Complexes Bearing 4,5,6,7-Tetrahydroisoindol-2-ide-Based PNP-Type Pincer Ligand

Kato, Takeru; et al, Chemistry - An Asian Journal, 2019, 14(12), 2097-2101

Production Method 6

76-09-5

96-54-8

953040-54-5

Reaction Conditions

1.1 Reagents: Aluminum chloride ,  (T-4)-Trichloro(N,N,4-trimethylbenzenamine)boron Solvents: Dichloromethane ;  3 h, 20 °C
1.2 Solvents: Triethylamine ;  0 - 5 °C; 1 h, 20 °C

Reference

Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis

Bagutski, Viktor; Del Grosso, Alessandro; Carrillo, Josue Ayuso; Cade, Ian A.; Helm, Matthew D.; et al, Journal of the American Chemical Society, 2013, 135(1), 474-487

Production Method 7

953040-54-5

Reaction Conditions

Reference

Hpk1 inhibitor and application thereof in medicine

, World Intellectual Property Organization, , ,

Production Method 8

25015-63-8

96-54-8

953040-54-5

850567-47-4

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Borate(1-), [2-(diethylamino)phenyl]trifluoro-, hydrogen (1:1), (T-4)- ;  2 h, 80 °C

Reference

Metal-Free Borylation of Heteroarenes Using Ambiphilic Aminoboranes: On the Importance of Sterics in Frustrated Lewis Pair C-H Bond Activation

Legare Lavergne, Julien; Jayaraman, Arumugam; Misal Castro, Luis C.; Rochette, Etienne; Fontaine, Frederic-Georges, Journal of the American Chemical Society, 2017, 139(41), 14714-14723

Production Method 9

76-09-5

96-54-8

953040-54-5

850567-47-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Aluminum chloride ,  2-Chloro-1,3,2-benzodioxaborole Solvents: Dichloromethane ;  20 °C
1.2 20 h, 20 °C
1.3 Reagents: Triethylamine ;  1 h, 20 °C

Reference

Pinacol boronates by direct arene borylation with borenium cations

Del Grosso, Alessandro; et al, Angewandte Chemie, 2011, 50(9), 2102-2106

Production Method 10

76-09-5

96-54-8

953040-54-5

1278579-60-4

850567-47-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Aluminum chloride ,  2-Chloro-1,3,2-benzodioxaborole Solvents: Dichloromethane ;  20 °C
1.2 192 h, 20 °C
1.3 Reagents: Triethylamine ;  1 h, 20 °C

Reference

Pinacol boronates by direct arene borylation with borenium cations

Del Grosso, Alessandro; et al, Angewandte Chemie, 2011, 50(9), 2102-2106

1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole Raw materials

• 2,3-Dimethylbutane-2,3-diol
• Bis(pinacolato)diborane
• Pinacolborane
• N-Methylpyrrole
• 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole

1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole Preparation Products

• 1-Methyl-1H-pyrrole-2,4-diboronic acid, pinacol ester (1278579-60-4)
• 1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole (850567-47-4)
• 1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole (953040-54-5)

• 1. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 2. Emerging investigator series: heterogeneous reactions of sulfur dioxide on mineral dust nanoparticles: from single component to mixed components?
  Tao Wang,Yangyang Liu,Yue Deng,Hongbo Fu,Jianmin Chen Environ. Sci.: Nano, 2018,5, 1821-1833
• 3. Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines?
  Thi Thu Tram Nguyen,Thanh Binh Nguyen Org. Biomol. Chem., 2021,19, 6015-6020
• 4. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 5. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625

• 329214-79-1(3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)
• 439813-86-2(1-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrrole)
• 2223030-16-6(1-propyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole)
• 439813-84-0(1-(1-Methylethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole)
• 1012085-50-5(3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine)
• 214360-77-7(3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole)
• 2223040-61-5(1-isobutyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole)
• 903499-35-4(1-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 683229-61-0(1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 1174718-91-2(1-Acetylpyrrole-3-boronic Acid Pinacol Ester)