Réaction #1966363

Équation de réaction

2-bromo-4-methyl-thiazole-5-carboxylic acid

3-(aminomethyl) pyridine

benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

N,N-diisopropylethylamine

→

2-bromo-4-methyl-thiazole-5-carboxylic acid (pyridine-3-ylmethyl)-amide

Rendement 96.1%

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (300 mL) and brine (2×200 mL)
2. 2
   SéchageThe organic phase was dried (Na2SO4)
3. 3
   Autreevaporated
4. 4
   AutreThe residue was purified by flash chromatography over silica gel (methylene chloride:methanol, 95:5)

Mode opératoire

To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid (10.0 g, 45.0 mmol) in methylene chloride (200 mL) was added 3-(aminomethyl) pyridine (5.05 mL, 49.5 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 21.9 g, 49.5 mmol) and N,N-diisopropylethylamine (15.7 mL, 90.1 mmol). The mixture was stirred under nitrogen at room temperature for 16 hr, then diluted with methylene chloride (300 mL), washed with water (300 mL) and brine (2×200 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography over silica gel (methylene chloride:methanol, 95:5) to provide 2-bromo-4-methyl-thiazole-5-carboxylic acid (pyridine-3-ylmethyl)-amide as a yellow solid (13.5 g, 96% yield). MS (M+H)+=313; Rt=1.01 min.

Source