Production Method 1

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: (SP-4-3)-rel-(Methanesulfonato-κO)[2′-[(R)-methylamino-κN][1,1′-biphenyl]-2-yl-κ… Solvents: 2-Methyltetrahydrofuran ;  24 h, 90 °C

Reference

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Wang, Xin; Liu, Wei-Gang; Tung, Chen-Ho ; Wu, Li-Zhu ; Cong, Huan, Organic Letters, 2019, 21(20), 8158-8163

Production Method 2

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  rt → 85 °C; overnight, 85 °C

Reference

Preparation of substituted indole compound as 5-hydroxytryptamine reuptake inhibitor

, World Intellectual Property Organization, , ,

Production Method 3

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  3 h, 145 °C

Reference

Improvement of aqueous solubility of lapatinib-derived analogues: identification of a quinolinimine lead for human African trypanosomiasis drug development

Bachovchin, Kelly A.; Sharma, Amrita; Bag, Seema; Klug, Dana M.; Schneider, Katherine M.; et al, Journal of Medicinal Chemistry, 2019, 62(2), 665-687

Production Method 4

57260-71-6

73183-34-3

32779-36-5

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetonitrile ;  25 °C; 6 h, 100 °C; 100 °C → 25 °C
1.2 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  25 °C; 6 h, 80 - 90 °C; 90 °C → 25 °C

Reference

Preparation of benzothiazoles and aza-analogues as antibacterial agents

, World Intellectual Property Organization, , ,

Production Method 5

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dimethyl sulfoxide ;  4 h, 80 °C; overnight, 100 °C

Reference

Preparation of pyrazolopyrimidine derivatives or analogs thereof as CCR4 function modulators

, Japan, , ,

Production Method 6

1003845-08-6

57260-71-6

940284-98-0

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Solvents: Ethanol ;  3 h, 80 °C

Reference

Heterobifunctional compounds for degradation of tropomyosin receptor kinase and their preparation

, World Intellectual Property Organization, , ,

Production Method 7

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  17 h, 120 °C

Reference

Preparation of thiazolidine derivatives as Pim inhibitors

, World Intellectual Property Organization, , ,

Production Method 8

780705-64-8

73183-34-3

940284-98-0

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 ;  30 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 9

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Solvents: 1,4-Dioxane ;  10 min, rt
1.2 Catalysts: Dichlorobis(triphenylphosphine)palladium ;  overnight, 95 °C

Reference

Preparation of azaindoles as aurora kinase inhibitors for the treatment of cancer

, United States, , ,

Production Method 10

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  16 h, 90 °C

Reference

Preparation of substituted imidazo[1,2-a]pyridin-3-amines as autotaxin inhibitors

, United States, , ,

Production Method 11

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  2 h, 100 °C

Reference

Preparation of triazole-based compounds as nuclear export protein inhibitor

, China, , ,

Production Method 12

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  16 h, 70 °C

Reference

Preparation of substituted nitrogen containing heterocyclic derivatives useful as PCSK9 inhibitors for the treatment of hyperlipidemia

, World Intellectual Property Organization, , ,

Production Method 13

374930-88-8

185990-03-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium methoxide Solvents: Methyl ether ;  1 h, 30 °C

Reference

Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies

Yamamoto, Eiji; Ukigai, Satoshi; Ito, Hajime, Chemical Science, 2015, 6(5), 2943-2951

Production Method 14

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dimethyl sulfoxide ;  overnight, 120 °C

Reference

Preparation of heterocyclic compounds as CCR4 or TARC and/or MDC function regulators

, Japan, , ,

Production Method 15

73183-34-3

374930-88-8

940284-98-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tricyclohexylphosphine ,  Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  5 h, rt → 100 °C

Reference

Preparation of condensed thiazoles as antibacterial agents

, World Intellectual Property Organization, , ,

Production Method 16

940284-98-0

Reaction Conditions

Reference

Preparation of substituted pyrazolo[1,5-a]pyridines as inhibitors of FGFR tyrosine kinases for the treatment of FGFRs-mediated diseases

, World Intellectual Property Organization, , ,

Production Method 17

940284-98-0

Reaction Conditions

Reference

Preparation of indazolones as modulators of TNF signaling

, World Intellectual Property Organization, , ,

Tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate Raw materials

• 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
• N-Boc-piperazine
• 1-N-Boc-4-pyriMidin-2-yl-piperazine
• Bis(pinacolato)diborane
• Tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate
• dimethyl(phenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
• 5-Bromo-2-chloropyrimidine

Tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate Preparation Products

• Tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate (940284-98-0)

• 1. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 2. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 3. Evolving better nanoparticles: Genetic algorithms for optimising cluster geometries
  Dalton Trans., 2003, 4193-4207
• 4. 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
• 5. 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

• 1350562-08-1(Tert-butyl N-[[1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]piperidin-4-yl]methyl]carbamate)
• 1632498-00-0((S)-Tert-butyl 3-methyl-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]piperazin-1-carboxylate)
• 1190423-36-9(tert-butyl N-[(tert-butoxy)carbonyl]-N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]carbamate)
• 1448461-87-7([2-(4-tert-butoxycarbonylpiperazin-1-yl)pyrimidin-5-yl]boronic acid)
• 1356464-60-2(Carbamic acid, N-[3-[[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinyl]amino]propyl]-, 1,1-dimethylethyl ester)
• 1032758-88-5(tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate)
• 1202805-38-6(Tert-butyl 4-[[[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]amino]methyl]piperidine-1-carboxylate)
• 1202805-35-3(Tert-butyl 4-[[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]amino]piperidine-1-carboxylate)
• 1202805-34-2(Tert-butyl N-[1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]pyrrolidin-3-yl]carbamate)
• 1202805-37-5(tert-butyl N-{1-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ylpiperidin-4-yl}carbamate)