7-Azaindole-5-boronic acid pinacol ester
- Product Name
- 7-Azaindole-5-boronic acid pinacol ester
- CAS No.
- 754214-56-7
- Chemical Name
- 7-Azaindole-5-boronic acid pinacol ester
- Synonyms
- EOS-60660;7-Azaindole-5-boronic aci...;7-Azaindole-5-boronic acid pinacol ester;7-Azaindole-5-boronoc acid pinacol ester;5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1;Pyrrolo[2,3-b)pyridine-5-boronic acid,pinacol ester;Pyrrolo[2,3-b]pyridin-5-ylboronic acid pinacol ester;1H-Pyrrolo[2,3-B]pyridine-5-boronic acid pinacol ester;7-Azaindole-5-boronic acid pinacol ester ISO 9001：2015 REACH;5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
- CBNumber
- CB0297862
- Molecular Formula
- C13H17BN2O2
- Formula Weight
- 244.1
- MOL File
- 754214-56-7.mol
7-Azaindole-5-boronic acid pinacol ester Property
- Melting point:
- 242-242.5°C
- Density
- 1.15±0.1 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- Soluble in methanol, ethanol and THF.
- pka
- 13.88±0.40(Predicted)
- form
- solid
- Appearance
- White to off-white Solid
- Sensitive
- Air Sensitive
- InChI
- InChI=1S/C13H17BN2O2/c1-12(2)13(3,4)18-14(17-12)10-7-9-5-6-15-11(9)16-8-10/h5-8H,1-4H3,(H,15,16)
- InChIKey
- QXOZTDXLAMPSBE-UHFFFAOYSA-N
- SMILES
- C12NC=CC1=CC(B1OC(C)(C)C(C)(C)O1)=CN=2
- CAS DataBase Reference
- 754214-56-7
Safety
- Hazard Codes
- Xi,T,Xn
- Risk Statements
- 25-20/21/22-36/37/38
- Safety Statements
- 45-36-22-37-26
- WGK Germany
- 3
- HazardClass
- IRRITANT
- HS Code
- 29339980
N-Bromosuccinimide Price
- Product number
- 748862
- Product name
- 7-Azaindole-5-boronic acid pinacol ester
- Purity
- 97%
- Packaging
- 250mg
- Price
- $67.8
- Updated
- 2023/06/20
- Product number
- 748862
- Product name
- 7-Azaindole-5-boronic acid pinacol ester
- Purity
- 97%
- Packaging
- 1g
- Price
- $248
- Updated
- 2023/06/20
- Product number
- ADE000890
- Product name
- 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
- Purity
- Aldrich
- Packaging
- 1g
- Price
- $817
- Updated
- 2025/07/31
- Product number
- P991923
- Product name
- 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
- Packaging
- 500mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- 5H60-1-01
- Product name
- 7-Azaindole-5-boronic acid, pinacol ester
- Purity
- 97%
- Packaging
- 1g
- Price
- $125
- Updated
- 2021/12/16
7-Azaindole-5-boronic acid pinacol ester Chemical Properties,Usage,Production
Chemical Properties
White powder
Uses
7-Azaindole-5-boronic acid pinacol ester is used as pharmaceutical intermediate.
Synthesis
866546-07-8
76-09-5
121-43-7
754214-56-7
Step 1: 5-Chloro-1H-pyrrolo[2,3-b]pyridine (3 g, 0.02 mol) was dissolved in dichloromethane (50 ml) and triethylamine (0.20 mol) and tert-butyldimethylchlorosilane (0.2 mol) were added sequentially under stirring. The reaction mixture was stirred overnight at room temperature and the reaction was monitored by thin layer chromatography (TLC) until completion. Upon completion of the reaction, it was quenched by adding 50 ml of water and 10 ml of 0.1 mol/L dilute hydrochloric acid. The organic phase was separated and washed sequentially with 50 ml of water, 50 ml of saturated sodium carbonate solution and 50 ml of saturated sodium chloride solution. After evaporating the solvent of dichloromethane phase, the residue was washed with acetone three times and dried to obtain a yellow solid. Step 2: The yellow solid obtained in step 1 was dissolved in 50 ml of tetrahydrofuran (THF), keeping the temperature of the reaction system at -5°C. Sodium carbonate (0.53 g, 0.005 mol) was added, then trimethyl borate (4.6 ml, 0.04 mol) was added slowly dropwise. After addition, the reaction mixture was warmed up to room temperature and the solvent was evaporated under reduced pressure to obtain a yellow oily substance. Step 3: To the yellow oily substance obtained in step 2, 80 ml of ethyl acetate and pinacol (0.02 mol) were added and the reaction was refluxed. The reaction was monitored by TLC until completion. After evaporation of the solvent, the residue was dissolved in 100 ml of acetone, stirred and filtered. The filtrate was concentrated to dryness to give a colorless oil. Step 4: The colorless oily material obtained in step 3 was dissolved in 50 ml of ether, 30 ml of 0.1 mol/L dilute hydrochloric acid was added and stirred overnight. After evaporating the solvent, the residue was extracted with 30 ml of ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was further purified by 1:1 (v/v) chloroform-crystallization (20 ml) to give a white solid. The final product was 7-azaindole-5-boronic acid pinacol ester (2.78 g, HPLC purity 99.8%) in 56.8% overall yield.
References
[1] Patent: CN104478909, 2017, B. Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020; 0021-0036
7-Azaindole-5-boronic acid pinacol ester Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 7-Azaindole-5-boronic acid pinacol ester manufacturers
- Product
- 7-Azaindole-5-boronic acid pinacol ester 754214-56-7
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 tons
- Release date
- 2021-10-18
- Product
- 5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE 754214-56-7
- Price
- US $500.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2018-08-04