Réaction #1583812

Équation de réaction

ethyl acetate

2-isopropyl-4-(4-fluorophenyl)-1,3-thiazole

4-bromo-2-methylpyridine

potassium acetate

→

4-[4-(4-Fluorophenyl)-2-isopropyl-1,3-thiazol-5-yl]-2-methylpyridine

Solvants

DMA

Conditions de réaction

Traitement

1. 1
   Filtrationthe reaction mixture is filtered through a silica gel cartridge
2. 2
   workup.ADDITION10 ml of water are added to the filtrate
3. 3
   AutreThe organic phase is separated off
4. 4
   Lavagewashed once more with 10 ml of water
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Mode opératoire

Under argon, 200 mg (0.90 mmol) of 2-isopropyl-4-(4-fluorophenyl)-1,3-thiazole, 77 mg (0.45 mmol) of 4-bromo-2-methylpyridine, 133 mg (1.35 mmol) of potassium acetate and 0.4 mg (2 μmol) of palladium(II) acetate in 5 ml of DMA are heated to 150° C. After 3 h, 50 ml of ethyl acetate are added and the reaction mixture is filtered through a silica gel cartridge. 10 ml of water are added to the filtrate. The organic phase is separated off, washed once more with 10 ml of water, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 115 mg (41%) of the desired product; 1H-NMR(DMSO-(D6) δ: 8.39 (d, 1H), 7.48 (m, 2H), 7.22 (m, 2H), 7.17 (s, 1H), 7.03 (d, 1H), 3.35 (m, 1H), 2.43 (s, 3H), 1.39 (d, 6H).

Source