5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE

Base Information

• Chemical Name: 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE
• CAS No.: 754214-56-7
• Molecular Formula: C13H17BN2O2
• Molecular Weight: 244.101
• Hs Code.: 29339980
• Mol file: 754214-56-7.mol

Synonyms:5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;

Chemical Property of 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE

Chemical Property:

• Melting Point: 242-242.5 °C
• Refractive Index: 1.573
• PKA: 13.88±0.40(Predicted)
• PSA: 47.14000
• Density: 1.154 g/cm³
• LogP: 1.86210
• Storage Temp.: ?20°C
• Sensitive.: Air Sensitive
• Solubility.: Soluble in methanol, ethanol and THF.

Purity/Quality:

99% ^*data from raw suppliers

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,Xn
• Statements: 25-20/21/22-36/37/38
• Safety Statements: 45-36-22-37-26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7-Azaindole-5-boronic acid pinacol ester is used as pharmaceutical intermediate.

Technology Process of 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE

There total 7 articles about 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.9%

bis(pinacol)diborane (73183-34-3) + 5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (754214-56-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield: 73.0%

→ 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (754214-56-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 5h; Reflux; Inert atmosphere;

Reference yield: 56.8%

5-chloro-1H-pyrrolo[2,3-b]pyridine (866546-07-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) + Trimethyl borate (121-43-7,63156-11-6) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (754214-56-7)

Guidance literature:

5-chloro-1H-pyrrolo[2,3-b]pyridine; With tert-butyldimethylsilyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃;

Trimethyl borate; With sodium carbonate; In tetrahydrofuran; dichloromethane; at -5 ℃;

2,3-dimethyl-2,3-butane diol; Temperature; Further stages;

upstream raw materials:

bis(pinacol)diborane

5-bromo-1H-pyrrolo[2,3-b]pyridine

7-Azaindole

5-chloro-1H-pyrrolo[2,3-b]pyridine

Downstream raw materials:

2-chloro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

1-cyclopentyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

7-Azaindole

C₃₀H₂₄N₆O₃

Refernces

• 1、 -. "AZAINDOLE DERIVATIVE AND USE THEREOF AS FGFR AND C-MET INHIBITOR". Paragraph 0117; 0121. . Retrieved 2021/05/29.
• 2、 Wang, Xin,Liu, Wei-Gang,Tung, Chen-Ho,Wu, Li-Zhu,Cong, Huan. "A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions". supporting information. p. 8158 - 8163. Retrieved 2019/09/07.