反应详情

N-Ethyl-N′-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]urea (Intermediate 1, 0.20 g, 0.69 mmol), methyl 2-bromo-1,3-thiazole-5-carboxylate (0.152 g, 0.69 mmol), tetrakis triphenyl phosphine palladium (0.08 g, 0.069 mmol), and cesium carbonate (0.245 mg, 0.754 mmol) were taken in a microwave vial and degassed with argon. Then dioxane:water (4:1, 3 mL) was added to it and microwaved at 110° C. for half an hour. The reaction mixture was partitioned between water and EtOAc and layers separated. The organic layer was washed with sat. sodium bicarbonate solution, water, brine and dried over magnesium sulfate. The solvent was removed and the residue was purified by flash chromatography eluting with 2% MeOH in DCM to 3% MeOH in DCM. MS (ESP): 307 (M+H+) for C13H14N4O3S; NMR: 1.09 (t, 3H), 3.16-3.22 (m, 2H), 3.86 (s, 3H), 7.60 (d, 1H), 7.79 (t, 1H), 8.27 (dd, 1H), 8.49 (s, 1H), 8.83 (s, 1H), 9.56 (s, 1H).

1. customdegassed with argon
2. additionThen dioxane:water (4:1, 3 mL) was added to it
3. custommicrowaved at 110° C. for half an hour
4. customThe reaction mixture was partitioned between water and EtOAc and layers
5. customseparated
6. washThe organic layer was washed with sat. sodium bicarbonate solution, water, brine
7. dry with materialdried over magnesium sulfate
8. customThe solvent was removed
9. customthe residue was purified by flash chromatography
10. washeluting with 2% MeOH in DCM to 3% MeOH in DCM