Production Method 1

2639372-89-5

946427-03-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ;  rt → 25 °C; 2 h, 25 °C
1.2 Reagents: Water

Reference

Crisaborole intermediate, preparation method and application thereof in preparing crisaborole

, China, , ,

Production Method 2

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Tetrabutylammonium fluoride Solvents: Acetone ,  Acetonitrile ,  Water ;  39 min, -5 °C

Reference

Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions

Chen, Kai; Cheung, Man Sing; Lin, Zhenyang; Li, Pengfei, Organic Chemistry Frontiers, 2016, 3(7), 875-879

Production Method 3

14472-14-1

25015-63-8

946427-03-8

Reaction Conditions

1.1 Catalysts: Tricyclohexylphosphine ,  Bis(dibenzylideneacetone)palladium Solvents: 1,4-Dioxane ;  1.5 h, rt
1.2 Reagents: Potassium acetate ;  20 h, rt → 80 °C; 80 °C → rt

Reference

Arylpyrazole derivatives as FXR agonists and their preparation, pharmaceutical compositions and use in the treatment of dyslipidemia and related diseases

, World Intellectual Property Organization, , ,

Production Method 4

14472-14-1

25015-63-8

946427-03-8

Reaction Conditions

1.1 Reagents: Tricyclohexylphosphine Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane ;  1.5 h, rt
1.2 Reagents: Potassium acetate ;  20 h, rt → 80 °C; cooled

Reference

Preparation of 3-phenylisoxazole derivatives for treatment of dyslipidemia

, World Intellectual Property Organization, , ,

Production Method 5

76-09-5

493035-82-8

946427-03-8

Reaction Conditions

1.1 Solvents: Toluene ;  6 h, rt → 110 °C

Reference

Preparation of diol- or boron-containing pyrimidine and imidazo[1,2-a]pyridine, and quinoline derivatives as Bcr-abl tyrosine-kinase ligands capable of dimerizing in an aqueous solution, and methods of using same

, World Intellectual Property Organization, , ,

Production Method 6

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

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

Reference

Preparation of 3-oxo-2,3-dihydropyridazin-4-ylurea derivatives as PDE4 inhibitors

, World Intellectual Property Organization, , ,

Production Method 7

946427-03-8

Reaction Conditions

Reference

Preparation of 3-oxo-2,3-dihydropyridazin-4-ylurea derivatives as PDE4 inhibitors

, European Patent Organization, , ,

Production Method 8

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  24 h, 90 °C

Reference

Preparation of biphenyl compounds useful as immunomodulators for treatment of cancer, infectious diseases, and septic shock

, World Intellectual Property Organization, , ,

Production Method 9

76-09-5

493035-82-8

946427-03-8

Reaction Conditions

1.1 Solvents: Diethyl ether ;  18 h, rt

Reference

Preparation of labeled aromatic amino acids via late-stage 18F-fluorination of chiral nickel and copper complexes

Craig, Austin; Kolks, Niklas; Urusova, Elizaveta A.; Zischler, Johannes; Brugger, Melanie; et al, Chemical Communications (Cambridge, 2020, 56(66), 9505-9508

Production Method 10

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  rt → 95 °C; 6 h, 95 °C

Reference

Preparation of pyridine derivatives as tubulin-src kinase double target inhibitor and antitumor agents

, China, , ,

Production Method 11

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Sodium acetate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Polyethylene glycol ;  10.0 h, 90 °C

Reference

An improved procedure for the synthesis of arylboronates by palladium-catalyzed coupling reaction of aryl halides and bis(pinacolato)diboron in polyethylene glycol

Lu, Jie; Guan, Zhong-Zhi; Gao, Jian-Wu; Zhang, Zhan-Hui, Applied Organometallic Chemistry, 2011, 25(7), 537-541

Production Method 12

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Potassium acetate Solvents: Dimethylformamide ;  rt
1.2 Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… ;  19 h, 80 °C; 80 °C → rt
1.3 Reagents: Water

Reference

Preparation of isoxazole compounds as therapeutic farnesoid X receptor agonists

, United States, , ,

Production Method 13

14472-14-1

25015-63-8

946427-03-8

Reaction Conditions

1.1 Catalysts: Tricyclohexylphosphine ,  Bis(dibenzylideneacetone)palladium Solvents: 1,4-Dioxane ;  1.5 h, rt
1.2 Reagents: Potassium acetate ;  20 h, rt → 80 °C; 80 °C → rt

Reference

Aryltriazole derivatives as FXR modulators and their preparation, pharmaceutical compositions and use in the treatment of dyslipidemia and related diseases

, World Intellectual Property Organization, , ,

Production Method 14

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  15 h, 90 °C

Reference

Preparation of pyrrolopyridazine compounds as kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 15

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethylformamide ;  18 h, 80 °C

Reference

1,7-Naphthyridine derivatives as p38 MAP kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 16

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: Dimethylformamide ;  18 h, 80 °C; cooled

Reference

Preparation of pyridin-3-amine derivatives as p38 mitogen-activated protein kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 17

14472-14-1

73183-34-3

946427-03-8

Reaction Conditions

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

Reference

Synthesis of substituted asymmetrical biphenyl amino esters as alpha helix mimetics

Williams, Anna B.; Hanson, Robert N., Tetrahedron, 2012, 68(27-28), 5406-5414

Production Method 18

14472-14-1

25015-63-8

946427-03-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: Toluene ;  5 h, 80 °C
1.2 Reagents: Methanol

Reference

Preparation of arylboronates as inhibitors of fatty acid amide hydrolase

, World Intellectual Property Organization, , ,

Production Method 19

946427-03-8

Reaction Conditions

Reference

Use of Intramolecular 1,5-Sulfur-Oxygen and 1,5-Sulfur-Halogen Interactions in the Design of N-Methyl-5-aryl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine SMN2 Splicing Modulators

Axford, Jake; Sung, Moo Je; Manchester, John; Chin, Donovan; Jain, Monish; et al, Journal of Medicinal Chemistry, 2021, 64(8), 4744-4761

3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol Raw materials

• 2,3-Dimethylbutane-2,3-diol
• (4-hydroxy-2-methylphenyl)boronic acid
• Trimethyl[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]silane
• 4-Bromo-3-methylphenol
• Bis(pinacolato)diborane
• Pinacolborane

3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol Preparation Products

• 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (946427-03-8)

• 1. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 2. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
  Bo Cao,Yin Wei Chem. Commun., 2018,54, 2870-2873
• 3. An integrated microfluidic platform for sensitive and rapid detection of biological toxins?
  Robert J. Meagher,Anson V. Hatch,Ronald F. Renzi,Anup K. Singh Lab Chip, 2008,8, 2046-2053
• 4. An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS?
  Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” Kim Lab Chip, 2006,6, 1213-1219
• 5. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068

• 1375301-93-1(2-(2-Isopropyl-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 914675-53-9(1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-[2,4,6-tris(1-methylethyl)phenyl]-)
• 948592-58-3(2-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol)
• 507462-90-0(3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol)
• 1196985-65-5(4-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol)
• 852110-33-9(4,4,5,5-tetramethyl-2-2-(propan-2-yl)phenyl-1,3,2-dioxaborolane)
• 1029439-74-4(5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile)
• 214360-68-6(2-(4-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1208459-72-6(2-(4-methoxy-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1905413-57-1(3-Ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol)