Réaction #90367

Équation de réaction

3-Amino-5-bromo pyridine

pyridine

isobutyryl chloride

→

N-(5-bromopyridin-3-yl)isobutyramide

Rendement 71.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water
2. 2
   ExtractionThe organic extract
3. 3
   Autrewas dried
4. 4
   Concentrationconcentrated
5. 5
   Autrepurified by column chromatography

Mode opératoire

3-Amino-5-bromo pyridine (XXX)(1 eq) was dissolved in DCM and cooled to 0° C. before adding pyridine (2.2 eq) and isobutyryl chloride (XXXI) (1.1 eq). The reaction mixture was stirred at r.t. for 15 h until TLC showed the reaction was complete. The reaction mixture was diluted with DCM and washed with water. The organic extract was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford N-(5-bromopyridin-3-yl)isobutyramide (XXXII) as a off white solid, (71% yield). 1H NMR (CDCl3) δ ppm 8.55-8.35 (m, 3H), 7.32 (s, 1H), 2.59-2.48 (m, 1H), 1.28-1.27 (d, 6H); ESIMS found C9H11BrN2O m/z 243.05(M+H).

Source