反应详情

To a 2 dram vial equipped with a stir bar and charged with the entirety of 5-(4-chloro-6-methylpyridin-2-yl)thiazole from step 1 was added CsF (200 mg, 1.32 mmol) and DMSO (0.7 mL). The vial was capped and then placed in a 140° C. heating block with stirring for 16 h. The reaction mixture was transfered to a 125 mL separatory funnel and was diluted with EtOAc (50 mL). The solution was twice washed with brine:water (25 mL:25 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford an amber solid residue. This material was subjected to silica gel chromatography (hexanes:EtOAc) to afford 5-(4-fluoro-6-methylpyridin-2-yl)thiazole as a colorless solid (7.1 mg, 21% over two steps). 1H-NMR (500 MHz, CDCl3) 8.84 (d, J=0.3 Hz, 1H), 8.32 (d, J=0.3 Hz, 1H), 7.22 (dd, J=9.3, 1.7 Hz, 1H), 6.82 (dd, J=9.2, 2.0 Hz, 1H), 2.59 (s, 3H); MS: MS m/z 195.2 (M++1).

1. customTo a 2 dram vial equipped with a stir bar
2. customThe vial was capped
3. customplaced in a 140° C.
4. temperatureheating block
5. customThe reaction mixture was transfered to a 125 mL separatory funnel
6. washThe solution was twice washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthen concentrated in vacuo
10. customto afford an amber solid residue