Methyl iodide → HCID 55141659, compound

Participants

Reaction Conditions

Reaction Steps

A dry round bottom flask containing 5-bromo-N-(3-methoxypropyl)-3-nitropyridin-2-amine (1.0 g, 3.45 mmol) in dry DMF (4.5 mL) was cooled to 0° C., then sodium hydride, 60% dispersion in mineral oil (0.28 g, 7.02 mmol) was added carefully in portions. The mixture was stirred at 0° C. for 15 min, then iodomethane (0.66 mL, 10.6 mmol) was added dropwise. Upon complete addition, the mixture was allowed to warm to 23° C. After 19 h, the reaction was carefully diluted with water then extracted five times with EtOAc. The organic extraction was then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-25% EtOAc in hexanes) to afford a light yellow oil as 5-bromo-N-(3-methoxy propyl)-N-methyl-3-nitropyridin-2-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.31 (1H, d, J=2.3 Hz), 8.21 (1H, d, J=2.3 Hz), 3.79 (2H, m), 3.47 (2H, m), 3.33 (3H, s), 2.86 (3H, s), 2.01 (2H, m).

Provenance & Evidence