Réaction #2154522

Équation de réaction

3-(aminomethyl)pyridine

2-bromo-4-methylthiazole-5-carboxylic acid

4-methylmorpholine

isobutyl chloroformate

→

2-bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Rendement 52.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature for 17 hours
2. 2
   Concentrationconcentrated in vacuo
3. 3
   AutreThe residue was purified by column chromatography

Mode opératoire

To a solution of 2-bromo-4-methylthiazole-5-carboxylic acid (10.00 g, 45.00 mmol) and 4-methylmorpholine (6.5 mL, 59.0 mmol) in tetrahydrofuran (150 mL) was added isobutyl chloroformate (6.5 mL, 49.6 mmol) at 0° C. The resulting mixture was stirred at room temperature for 1 hour and 3-(aminomethyl)pyridine (5.2 mL, 51.4 mmol) was added. The reaction mixture was stirred at ambient temperature for 17 hours, and then concentrated in vacuo. The residue was purified by column chromatography to afford 2-bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide in 52% yield (7.3 g): 1H NMR (300 MHz, CDCl3) δ 8.39-8.80 (m, 2H), 7.80-7.72 (m, 1H), 7.40-7.35 (m, 1H), 6.47 (br s, 1H), 4.60 (d, J=6.0 Hz, 2H), 2.64 (s, 3H); MS (ES+) m/z 312.1 (M+1), 314.1 (M+1).

Source