반응 #85434

반응 방정식

compound 145-H

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

benzenesulfonyl chloride

benzenesulfonyl chloride

→

solid

수율 36.0%

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

수율 36.0%

용매

pyridine

반응 조건

후처리

1. 1
   온도the reaction mixture was heated at 50° C. for an additional 16 h
2. 2
   기타The solvent was evaporated in vacuo
3. 3
   workup.DISSOLUTIONthe residue dissolved in dichloromethane
4. 4
   세척washed with aqueous sodium bicarbonate
5. 5
   추출extracted with dichloromethane
6. 6
   기타the organic layer was evaporated in vacuo

실험 절차

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+).

출처