Production Method 1

55052-28-3

73183-34-3

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Tris(dibenzylideneacetone)dipalladium ,  2-(Dicyclohexylphosphino)biphenyl Solvents: 1,2-Dimethoxyethane ;  5 h, 90 °C

Reference

Preparation of thienopyrimidine as CDC7 kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 2

55052-28-3

73183-34-3

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate ,  2-(Dicyclohexylphosphino)biphenyl Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  3 h, reflux

Reference

Oxazoles and related compounds as FLT3 kinase inhibitors and their preparation and use in the treatment of autoimmune disease

, World Intellectual Property Organization, , ,

Production Method 3

55052-28-3

73183-34-3

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate ,  2-(Dicyclohexylphosphino)biphenyl Solvents: 1,4-Dioxane ;  5 h, 100 °C; 100 °C → rt

Reference

Preparation of heteroarylmorpholinyltriazine derivatives for use as kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 4

73183-34-3

348640-06-2

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  3 h, 90 °C

Reference

Preparation of isoquinolines as inhibitors of HPK1 useful for treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 5

73183-34-3

348640-06-2

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Isopropyl acetate ;  22 h, 85 - 90 °C

Reference

Processes and intermediates for the preparation of a nonracemic sulfimidoylpyrimidinyl pyrrolopyridine

, World Intellectual Property Organization, , ,

Production Method 6

73183-34-3

348640-06-2

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  25 °C → 95 °C; 12 h, 95 °C

Reference

Development and Scale-up of a Route to ATR Inhibitor AZD6738

Goundry, William R. F. ; Dai, Kuangchu; Gonzalez, Miguel; Legg, Daniel; OKearney-McMullan, Anne; et al, Organic Process Research & Development, 2019, 23(7), 1333-1342

Production Method 7

73183-34-3

348640-06-2

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  18 h, 90 °C

Reference

Discovery of GSK1070916, a Potent and Selective Inhibitor of Aurora B/C Kinase

Adams, Nicholas D.; Adams, Jerry L.; Burgess, Joelle L.; Chaudhari, Amita M.; Copeland, Robert A.; et al, Journal of Medicinal Chemistry, 2010, 53(10), 3973-4001

Production Method 8

55052-28-3

73183-34-3

942919-26-8

Reaction Conditions

1.1 Reagents: Potassium acetate ,  2-(Dicyclohexylphosphino)biphenyl Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  3 h, reflux

Reference

Oxazoles and related compounds as tyrosine kinase inhibitors and their preparation and use in the treatment of kinase-mediated diseases

, World Intellectual Property Organization, , ,

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine Raw materials

• 4-Chloro-1H-pyrrolo[2,3-b]pyridine
• Bis(pinacolato)diborane
• 4-Bromo-7-azaindole

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine Preparation Products

• 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine (942919-26-8)

• 1. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
  Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
• 2. Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761
• 3. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 4. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 5. Fe3O4@PANI: a magnetic polyaniline nanomaterial for highly efficient and handy enrichment of intact N-glycopeptides??
  Zhizhen Lai,Mo Zhang,Jinyu Zhou,Tianjing Chen,Dan Li,Xuejing Shen,Jia Liu,Jiang Zhou,Zhili Li Analyst, 2021,146, 4261-4267

• 754214-56-7(5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine)
• 675576-26-8(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline (>85%))
• 1204742-76-6(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)imidazo[1,2-A]pyridine)
• 1222533-84-7(5-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine)
• 945256-29-1(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine)
• 943323-56-6(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine)
• 1072152-50-1(5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine)
• 1035458-54-8(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline)
• 1082947-07-6(7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline)
• 1198096-23-9(5-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine)