2-Amino-5-bromopyridine → N-(5-bromo-pyridin-2-yl)-2-methylsulfanyl-acetamide

(1 g, 5.78 mmol) 5-Bromopyridin-2-amine was dissolved in DMF (40 ml) and HATU (2.64 g, 6.94 mmol, 1.2 equiv.) was added. After 15 minutes at room temperature Hunig's Base (6.0 ml, 34.7 mmol, 6 equiv.) and 2-(methylthio)acetic acid (736 mg, 6.94 mmol, 1.2 equiv.) were added. The mixture was stirred for 72 hours at room temperature. The reaction mixture was evaporated and extracted three times with saturated Na2CO3 solution and three times with ethyl acetate. The organic layers were extracted three times with 1N HCl solution and evaporated to dryness. The crude product was suspended in pentane, filtered and the solid evaporated to dryness. The desired N-(5-bromo-pyridin-2-yl)-2-methylsulfanyl-acetamide (312 mg, 21% yield) was obtained as a yellow solid, MS: m/e=258.9/260.8 (M+H+).

1. customThe reaction mixture was evaporated
2. extractionextracted three times with saturated Na2CO3 solution and three times with ethyl acetate
3. extractionThe organic layers were extracted three times with 1N HCl solution
4. customevaporated to dryness
5. filtrationfiltered
6. customthe solid evaporated to dryness

ORD record

ord-ee4275569f79458bb2f86d683c897aef

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530472B2