3-Aminopyridine → HCID 22663597, compound

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.

1. washThe mixture was washed with 30 ml saturated sodium bicarbonate solution
2. extractionextracted with 15% isopropanol/dichloromethane
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD record

ord-9a70038bf5d841c2aaf75ca89f11873b

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800651B2