3-Aminopyridine → HCID 22663597, compound

Participants

Reaction Steps

A solution of 3-aminopyridine (2.15 g, 22.84 mmol) and ethanesulfonyl chloride (2.18 ml, 22.84 mmol) in dichloromethane (150 ml) was stirred for 20 h at room temperature. The mixture was washed with 30 ml saturated sodium bicarbonate solution and extracted with 15% isopropanol/dichloromethane. The organics were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give N-(ethanesulfonyl)-3-aminopyridine (2.15 g, as a crude solid. The solid was dissolved in N,N-dimethylformamide (50 ml) and treated with potassium carbonate (6.37 g, 22.8 mmol) and 3-iodobenzyl bromide (6.80 g, 22.8 mmol) with stirring at room temperature for 3 h. The mixture was diluted with ethyl acetate (150 ml) and washed four times with water (100 ml). The organics were separated, dried over sodium sulfate, filtered, and concentrated in vacuo to afford a crude residue. The residue was purified on a 200 g pad of silica eluting with 3% methanol/dichloromethane to afford the title compound. MS calcd. 402.3; MS (M+1) 403.1.

Provenance & Evidence