Benzenesulfonyl chloride → N-(5-bromopyridin-3-yl)benzenesulfonamide

Temperatur

0 °C

To a stirred solution of 5-bromo-3-pyridinamine (2 g, 11.56 mmol), triethylamine (6.6 mL, 47.39 mmol) in dichloromethane (40 mL) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred for 15 min and then benzenesulfonyl chloride (3.21 mL, 23.69 mmol) was added slowly to give a brown solution. The reaction mixture was stirred for 2 h at room temperature. Diluted with dichloromethane and then washed with saturated aqueous sodium chloride solution, separated the organic layer, dried over sodium sulphate, concentrated under high vacuum, light yellow solid obtained. The solid was dissolved in methanol (20 mL), cooled to 0° C., added 10N aqueous sodium hydroxide (20 mL) solution. The reaction mixture was stirred for 1 h and then distilled out methanol completely, extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound MS (M+1): 315.2.

1. customat 0° C.
2. customto give a brown solution
3. stirringThe reaction mixture was stirred for 2 h at room temperature
4. washwashed with saturated aqueous sodium chloride solution
5. customseparated the organic layer
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated under high vacuum, light yellow solid
8. customobtained
9. stirringThe reaction mixture was stirred for 1 h
10. distillationdistilled out methanol completely
11. extractionextracted with ethyl acetate
12. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
13. dry with materialdried over sodium sulphate
14. concentrationconcentrated under vacuum

ORD-Eintrag

ord-c82a664c5cd64b4ebbe5b9e75268f989

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09073929B2