Pyridine → HCID 58762618, compound

Participants

Reaction Steps

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).

Provenance & Evidence