反应详情

温度

90 °C

A mixture of commercially available methyl 2-bromoisonicotinate (2.750 g; 12.70 mmol), 5-methyl-2-(tributylstannyl)thiazole (4.942 g; 12.70 mmol), copper iodide CuI (242 mg; 1.27 mmol), and Pd(PPh3)4 (1.471 g; 1.27 mmol) in anh. DMF (55 ml) was heated to 90° C., under nitrogen, for 18 h. After cooling to rt, the reaction mixture was filtered over a pad of celite, and the separated solids were washed with AcOEt. The organic layer was washed with water and brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded methyl 2-(5-methylthiazol-2-yl)isonicotinate as an orange solid. LC-MS (conditions A): tR=0.74 min.; [M+H]+: 235.10 g/mol.

1. temperatureAfter cooling to rt
2. filtrationthe reaction mixture was filtered over a pad of celite
3. washthe separated solids were washed with AcOEt
4. washThe organic layer was washed with water and brine
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure
8. customPurification by FC (heptane/AcOEt=7/3)