Hydrochloric Acid → N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

Temperature

25 °C

To a 25 mL round-bottomed flask was added was added 5-bromo-2-chloropyridin-3-amine (1.50 g, 7.23 mmol, Asymchem, Morrisville, N.C.), pyridine (20.0 mL, 248 mmol) and methanesulfonyl chloride (2.8 mL, 36 mmol). The mixture was stirred at 25° C. for 48 h. The mixture was then concentrated in vacuo and the residue was treated with methanol (30 mL), 1,4-dioxane (30 mL) and potassium carbonate (10 g, 72 mmol) and stirred at 60° C. for 5 h. The mixture was poured into water (300 mL) and acidified to pH 5 using conc HCl. To the solution was added pH 4.8 buffer (100 mL, Teknova, 3 M sodium acetate solution pH adjusted to 4.8) and the solution was extracted with EtOAc (3×100 mL). The combined extracts were washed with water (1×100 mL), brine (100 mL) and then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (5 to 60% EtOAc/hexane) afforded a semi-solid that was washed with 10% EtOAc/hexane to afford the title compound as a tan solid (1.68 g, 81%). MS (ESI, positive ion) m/z: 285 (M(79Br)+1), 287 (M(81Br)+1).

1. additionTo a 25 mL round-bottomed flask was added
2. concentrationThe mixture was then concentrated in vacuo
3. stirringstirred at 60° C. for 5 h
4. extractionwas extracted with EtOAc (3×100 mL)
5. washThe combined extracts were washed with water (1×100 mL), brine (100 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated onto silica
8. customPurification by silica gel chromatography (5 to 60% EtOAc/hexane)
9. customafforded a semi-solid
10. washthat was washed with 10% EtOAc/hexane

ORD record

ord-5a4dfbea77534cbcbd8a9eb4645a2b90

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820665B2