Réaction #1966364

Équation de réaction

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

1H-pyrazole-5-boronic acid

potassium carbonate

→

4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridine-3-ylmethyl)amide

Rendement 87.7%

Solvants

toluene

water

ethanol

Conditions de réaction

Traitement

1. 1
   AutreThe resulting mixture was degassed three times
2. 2
   TempératureThe reaction mixture was cooled to room temperature
3. 3
   workup.ADDITIONdiluted with ethyl acetate (200 mL)
4. 4
   Lavagewashed with brine (2×100 mL)
5. 5
   SéchageThe organic phase was dried (Na2SO4)
6. 6
   Autreevaporated
7. 7
   AutreThe residue was recrystallized from ethyl acetate

Mode opératoire

To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid (pyridine-3-ylmethyl)-amide (5.0 g, 16.0 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added 1H-pyrazole-5-boronic acid (2.15 g, 19.2 mmol), Pd(PPh3)4 (1.85 g, 1.60 mmol), and potassium carbonate (6.64 g, 48.1 mmol). The resulting mixture was degassed three times and heated to 100° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed with brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was recrystallized from ethyl acetate to provide 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid (pyridine-3-ylmethyl)amide as a white solid (4.20 g, 85% yield).

Source