Reaktion #85434

Reaktionsgleichung

compound 145-H

3-Bromo-thieno[3,2-b]pyridin-2-ylamine hydrochloride

benzenesulfonyl chloride

benzenesulfonyl chloride

→

solid

Ausbeute 36.0%

N-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-benzenesulfonamide hydrochloride

Ausbeute 36.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated at 50° C. for an additional 16 h
2. 2
   SonstigeThe solvent was evaporated in vacuo
3. 3
   workup.DISSOLUTIONthe residue dissolved in dichloromethane
4. 4
   Waschenwashed with aqueous sodium bicarbonate
5. 5
   Extraktionextracted with dichloromethane
6. 6
   Sonstigethe organic layer was evaporated in vacuo

Vorschrift

To a solution of compound 145-H (0.46 g, 1.52 mmol) in pyridine (4.6 mL), cooled to 0° C., was added benzenesulfonyl chloride (0.206 mL, 1.60 mmol), and the reaction was heated to 50° C. for 72 h. Additional benzenesulfonyl chloride (0.412 mL, 3.20 mmol) was added and the reaction mixture was heated at 50° C. for an additional 16 h. The solvent was evaporated in vacuo, the residue dissolved in dichloromethane and washed with aqueous sodium bicarbonate. The aqueous layer was acidified with 1N HCl, extracted with dichloromethane, and the organic layer was evaporated in vacuo to afford a yellow solid (0.22 g, 36%) as a 1/3.5 mixture of the 3-bromo- and 3-chloro-substituted compounds, 145-Ia and 145-Ib, respectively. 1H-NMR (DMSO-d6): δ 7.1-7.2 (m, 1H), 7.4-7.6 (m, 3H), 7.8 (m, 2H), 8.1-8.2 (m, 1H), 8.25-8.35 (m, 1H); MS: m/z 465 and 509 (MH+).

Quelle