1-(Benzenesulfonyl)-3-bromo-1H-pyrrolo[2,3-b]pyridine synthesis
- Product Name:1-(Benzenesulfonyl)-3-bromo-1H-pyrrolo[2,3-b]pyridine
- CAS Number:880769-95-9
- Molecular formula:C13H9BrN2O2S
- Molecular Weight:337.19
74420-15-8
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Yield: 98%
Reaction Conditions:
Stage #1:3-bromo-1H-pyrrolo[2,3-b]pyridine with tetrabutylammomium bromide;sodium hydroxide in dichloromethane
Stage #2:benzenesulfonyl chloride in dichloromethane at 0 - 20; for 1 h;
Steps:
20 4.2.20. 3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (14)
4.2.20
3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (14)
In a heat dried and nitrogen purged round bottom flask, 13 (175 mg, 0.89 mmol), tetrabutylammonium bromide (10 mg, 0.03 mmol), finely grounded sodium hydroxide (107 mg, 2.67 mmol) and CH2Cl2 (5 mL) were mixed, stirred and cooled down to 0 °C in an ice bath, then benzene sulfonyl chloride (0.142 mL, 1.11 mmol) was added slowly.
The mixture was left to warm up to room temperature and was stirred at this temperature for 1 h.
The reaction was hydrolyzed with water (6 mL) and extracted by CH2Cl2 (twice).
The organic layer was washed with water and a saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to give an orange solid.
The crude product was triturated in pentane, filtered, washed with pentane and dried to give 294 mg of the expected product as an orange solid in 98% yield. 1H NMR (300 MHz, CDCl3) δ (ppm): 8.48 (dd, J = 1.5, 4.8 Hz, 1H), 8.24-8.17 (m, 2H), 7.82 (dd, J = 1.5, 8.0 Hz, 1H), 7.79 (s, 1H), 7.60 (dd, J = 7.5 Hz, 1H), 7.54-7.46 (m, 2H), 7.27 (dd, J = 4.8, 8.0 Hz, 1H).
References:
Baltus, Christine B.;Jorda, Radek;Marot, Christophe;Berka, Karel;Bazgier, Václav;Kryštof, Vladimír;Prié, Gildas;Viaud-Massuard, Marie-Claude [European Journal of Medicinal Chemistry,2016,vol. 108,p. 701 - 719]
![1H-Pyrrolo[2,3-b]pyridine, 1-(phenylsulfonyl)-](/CAS/GIF/143141-23-5.gif)
143141-23-5
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880769-95-9
70 suppliers
$20.00/250mg
271-63-6
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$9.00/5g
880769-95-9
70 suppliers
$20.00/250mg
98-09-9
339 suppliers
$12.00/25 g
880769-95-9
70 suppliers
$20.00/250mg