Reaction #90367

Reaction equation

3-Amino-5-bromo pyridine

pyridine

isobutyryl chloride

→

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

Yield 71.0%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   Washwashed with water
2. 2
   ExtractionThe organic extract
3. 3
   Otherwas dried
4. 4
   Concentrationconcentrated
5. 5
   Otherpurified by column chromatography

Procedure

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