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| | 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester Basic information | | Application |
| Product Name: | 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester | | Synonyms: | 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine;1-(Phenylsulfonyl)-7-Azaindole-3-boronic acid pinacol ester;1-Phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester;1-(Phenylsulfonyl)-7-Azai...;1-(Phenylsulfonyl)-7-azaindole-3-boronic acid, poinacol ester;1-(Benzenesulfonyl)-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine;1-(benzenesulfonyl)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrrolo[2,3-b]pyridine;1-(Phenylsulfonyl)-7-Azaindole-3-boronic acid pinacol | | CAS: | 886547-94-0 | | MF: | C19H21BN2O4S | | MW: | 384.26 | | EINECS: | | | Product Categories: | | | Mol File: | 886547-94-0.mol | ![1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester Structure](CAS/GIF/886547-94-0.gif) |
| | 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester Chemical Properties |
| Melting point | 355-360°C | | storage temp. | Storage temp. 2-8°C | | form | solid | | Appearance | White to light brown Solid | | InChI | 1S/C19H21BN2O4S/c1-18(2)19(3,4)26-20(25-18)16-13-22(17-15(16)11-8-12-21-17)27(23,24)14-9-6-5-7-10-14/h5-13H,1-4H3 | | InChIKey | KZANVIJXSQABKR-UHFFFAOYSA-N | | SMILES | CC1(C)OB(OC1(C)C)c2cn(c3ncccc23)S(=O)(=O)c4ccccc4 |
| WGK Germany | 3 | | HS Code | 2933998090 | | Storage Class | 13 - Non Combustible Solids |
| | 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester Usage And Synthesis |
| Application | 1-Benzenesulfonylpyrrolopyridine-3-boronate is a carboxylic acid ester derivative that has wide applications in organic synthesis. | | Synthesis | General procedure: 3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (4.2 g, 10.9 mmol), bis(pinacolato)diboron (5.6 g, 21.8 mmol), potassium acetate (3.2 g, 32.7 mmol) and Pd(dppf)Cl2-CH2Cl2 (788 mg, 0.982 mmol) The mixture in DMF (40 mL) was placed in a sealed tube and the reaction was stirred at 90 °C for 2 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature, cooled by the addition of ice water, and the pH was adjusted to 12-14 with 6N NaOH solution.Subsequently, the aqueous phase was extracted with dichloromethane (DCM). The aqueous phase was acidified to pH~1 with 6N HCl and then extracted again with DCM several times. All organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated to give 1-benzenesulfonyl pyrrolidinopyridine-3-boronate (4.2 g, quantitative yield) as a brown solid, which could be used in the subsequent reaction without further purification. lCMS analysis showed m/e 386 (boronate M + H)+, 303 (boronic acid M + H)+. | | References | [1] Patent: WO2007/76423, 2007, A2. Location in patent: Page/Page column 53 |
| | 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester Preparation Products And Raw materials |
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