Production Method 1

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  16 h, 80 °C

Reference

Preparation of indole compounds as androgen receptor modulators

, World Intellectual Property Organization, , ,

Production Method 2

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  rt → 100 °C; 8 h, 100 °C

Reference

Azaindolepyrimidinamine heterocyclic compound for treating ovarian and endometrial cancer, and its application

, World Intellectual Property Organization, , ,

Production Method 3

138343-77-8

25015-63-8

942070-47-5

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: Hexane ;  1 min, rt
1.2 5 h, rt

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

Production Method 4

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  6 h, rt → 100 °C

Reference

Preparation of condensed thiazoles as antibacterial agents

, World Intellectual Property Organization, , ,

Production Method 5

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  7 h, 110 °C

Reference

Preparation of substituted pyrazolo[1,5-a]pyrimidine-3-carboxamides as Tyk2 inhibitors and uses thereof

, World Intellectual Property Organization, , ,

Production Method 6

192189-18-7

25015-63-8

942070-47-5

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  3 h, 80 °C

Reference

Rapid synthesis of bis(hetero)aryls by one-pot Masuda borylation-Suzuki coupling sequence and its application to concise total syntheses of meridianins A and G

Merkul, Eugen; Schaefer, Elisabeth; Mueller, Thomas J. J., Organic & Biomolecular Chemistry, 2011, 9(9), 3139-3141

Production Method 7

192189-18-7

25015-63-8

942070-47-5

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  3 h, 80 °C

Reference

Design of Novel 3-Pyrimidinylazaindole CDK2/9 Inhibitors with Potent In Vitro and In Vivo Antitumor Efficacy in a Triple-Negative Breast Cancer Model

Singh, Umed; Chashoo, Gousia; Khan, Sameer U.; Mahajan, Priya; Nargotra, Amit ; et al, Journal of Medicinal Chemistry, 2017, 60(23), 9470-9489

Production Method 8

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  8 h, 100 °C

Reference

Discovery of novel and orally bioavailable CDK 4/6 inhibitors with high kinome selectivity, low toxicity and long-acting stability for the treatment of multiple myeloma

Yuan, Kai ; Kuang, Wenbin ; Chen, Weijiao; Ji, Minghui; Min, Wenjian; et al, European Journal of Medicinal Chemistry, 2022, 228,

Production Method 9

138343-77-8

73183-34-3

942070-47-5

Reaction Conditions

1.1 Catalysts: 3,4,7,8-Tetramethyl-1,10-phenanthroline ,  Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium Solvents: Tetrahydrofuran ;  1 h, 80 °C
1.2 Solvents: Tetrahydrofuran ;  22 h, rt

Reference

Iridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism

Larsen, Matthew A.; Hartwig, John F., Journal of the American Chemical Society, 2014, 136(11), 4287-4299

Production Method 10

192189-18-7

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethylformamide ;  2.5 h, 80 °C

Reference

Preparation of pyridinonyl PDK1 inhibitors

, World Intellectual Property Organization, , ,

Production Method 11

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,2-Dimethoxyethane ;  overnight, 80 °C

Reference

Preparation of five membered heterocyclic compounds as STING agonists

, China, , ,

Production Method 12

226085-17-2

73183-34-3

942070-47-5

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  overnight, 100 °C
1.2 Reagents: Water

Reference

Imidazo[1,2-a]pyrazine derivatives as CDK inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer

, World Intellectual Property Organization, , ,

tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate Raw materials

• Tert-Butyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• tert-Butyl 1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• 1-Boc-3-Iodo-7-azaindole
• Bis(pinacolato)diborane
• Pinacolborane

tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate Preparation Products

• tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (942070-47-5)

• 1. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119
• 2. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 3. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 4. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 5. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389

• 877060-60-1(tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate)
• 1174038-67-5(tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate)
• 942070-45-3(Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indole-1-carboxylate)
• 942070-54-4(tert-Butyl 3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate)
• 1370616-23-1(Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate)
• 1256360-07-2(1-(Isopropoxycarbonyl)pyrrole-3-boronic acid, pinacol ester)
• 1391926-50-3(tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate)
• 1073338-93-8(Tert-butyl 5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrrolo[2,3-b]pyridine-1-carboxylate)
• 935278-73-2(tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate)
• 1025719-14-5(1-BOC-5-bromopyrrolo2,3-bpyridine-3-boronic Acid Pinacol Ester)