反应详情

温度

100 °C

To a 140 mL pressure flask was added 5-bromophthaiazine (3.5 g, 17 mmol), palladium (II) acetate (0.98 g, 4.4 mmol), triphenylphosphine (1.3 g, 5.0 mmol), potassium acetate (2.1 g, 21 mmol), MeOH (20 mL) and DMF (20 mL). The flask was sealed and purged with CO (3×). The flask was charged with CO to 40 PSI and stirred at 100° C. 15 hours. The suspension was filtered through Celite, the cake was washed with MeOH, and the filtrate was concentrated. The residue was taken up in DCM and washed with saturated sodium bicarbonate (2×), saturated sodium chloride (2×) and water (2×). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was adsorbed on to a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column, eluting with a gradient of EtOAc in hexane to provide methyl phthalazine-5-carboxylate (1.0 g, 32%). LCMS (M+H) 189.2 calc. for C10H9N2O2 189.1. 1H NMR (400 MHz, CDCl3): δ ppm 4.05 (s, 3H) 8.06 (d, J=8.41 Hz, 1H) 8.51-8.56 (m, 1H) 8.71 (d, 1H) 9.64 (s, 2H).

1. customThe flask was sealed
2. custompurged with CO (3×)
3. additionThe flask was charged with CO to 40 PSI
4. custom15 hours
5. filtrationThe suspension was filtered through Celite
6. washthe cake was washed with MeOH
7. concentrationthe filtrate was concentrated
8. washwashed with saturated sodium bicarbonate (2×), saturated sodium chloride (2×) and water (2×)
9. dry with materialThe organic layer was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. custompurified by chromatography through a Redi-Sep pre-packed silica gel column
13. washeluting with a gradient of EtOAc in hexane