Ethyl Acetate → N-(5-Bromo-2-methylpyridin-3-YL)-N-(methylsulfonyl)methanesulfonamide

Temperature

100 °C

To a solution of 5-bromo-2-methylpyridin-3-amine (PharmaBlock) (2.000 g, 10.69 mmol) in pyridine (15.0 mL) was added 4-dimethylaminopyridine (Aldrich) (0.131 g, 1.069 mmol) and methanesulfonyl chloride (2.5 mL, 32.1 mmol). The resulting mixture was heated to 100° C. under N2 for 2 h. Reaction was cooled to rt. The reaction mixture was poured into the beaker which filled with EtOAc (50 ml) and hand stirred for 10 minutes. The organic layer was decanted into a round-bottom flask. The original mixture (black paste) was dissolved into DCM (3 ml) followed by adding EtOAc (20 ml) and hand stirred for 10 min and decanted to the same round-bottom flask that was mentioned earlier. The combined organic layers were concentrated in-vacuo. The crude product was purified by column chromatography (120 g, 10% to 20% acetone in hexanes) to afford the desired product as light brown solid (1.1 g). MS (ESI pos. ion) m/z: 342.8. 1H NMR (300 MHz, CDCl3) δ ppm 2.64 (s, 3H) 3.47 (s, 6H) 7.73 (d, J=2.05 Hz, 1H) 8.67 (d, J=2.05 Hz, 1H).

1. customReaction
2. temperaturewas cooled to rt
3. additionThe reaction mixture was poured into the beaker which
4. customThe organic layer was decanted into a round-bottom flask
5. dissolutionThe original mixture (black paste) was dissolved into DCM (3 ml)
6. additionby adding EtOAc (20 ml) and hand
7. stirringstirred for 10 min
8. customdecanted to the same round-bottom flask that
9. concentrationThe combined organic layers were concentrated in-vacuo
10. customThe crude product was purified by column chromatography (120 g, 10% to 20% acetone in hexanes)

ORD record

ord-684eb6e44f114b9d9ac5e2d64b442793

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772480B2