Pyridine → HCID 58762618, compound

Methane sulfonyl chloride (2.03 ml, 26 mmol) was added to a solution of 4-bromo-2-fluoroaniline (5.0 g, 26 mmol) and pyridine (2.12 ml, 26 mmol) in dichloromethane (100 ml) at 0° C. The reaction mixture was stirred for 1 hr, after which time it was partitioned between dichloromethane (100 ml) and 1N hydrochloric acid (100 ml). The organics were separated and dried over magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The crude oil was dissolved in dimethylformamide (50 mL) and treated with potassium carbonate (5.1 g, 37.5 mmol) followed by methyl iodide (2.33 ml, 37.4 mmol). The reaction mixture was stirred for 24 hrs after which time it was partitioned between diethylether (100 ml) and water (100 ml). The aqueous was extracted further with diethyl ether (2×100 ml). The combined organics were dried over magnesium sulfate, filtered and the solvent concentrated in vacuuo to afford the title compound as a brown oil (6.9 g). 1H NMR (CDCl3): δ 2.94 (s, 3H), 3.10 (s, 3H), 6.77 (t, J=4.96 Hz, 1H), 6.95 (d, J=4.96 Hz, 1H), 7.05 (m, 1H).

1. customafter which time it was partitioned between dichloromethane (100 ml) and 1N hydrochloric acid (100 ml)
2. customThe organics were separated
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto afford a yellow oil
7. stirringThe reaction mixture was stirred for 24 hrs after which time it
8. customwas partitioned between diethylether (100 ml) and water (100 ml)
9. extractionThe aqueous was extracted further with diethyl ether (2×100 ml)
10. dry with materialThe combined organics were dried over magnesium sulfate
11. filtrationfiltered
12. concentrationthe solvent concentrated in vacuuo

ORD record

ord-85ef9043b0b04f97a50500a4270aced6

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2