反应详情

温度

85 °C

A 500 mL RBF was charged with (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (20.00 g, 54.8 mmol), 2-fluoropyridin-3-ylboronic acid (13.89 g, 99 mmol) and sodium carbonate (23.22 g, 219 mmol). DMF (130 mL) was added and the mixture was stirred for 1 minute before tetrakis(triphenylphosphine) palladium (4.43 g, 3.83 mmol) and water (52.2 mL) were added. The mixture was capped with argon, equipped with a reflux condenser and heated at 85° C. for 16 hrs. The mixture was cooled to RT and the resulting yellow precipitate was filtered. The filtrate was diluted with water (200 mL) and saturated ammonium chloride (200 mL), leading to the formation of a white precipitate and a brown semisolid. The precipitate was filtered and the semisolid was triturated with water (˜200 mL) to provide a brown solid which was also filtered and washed with water. The combined solids were washed excessively with water and dried overnight under a stream of air to afford (S)-2-amino-4′-fluoro-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2′-ol as tan solid which was used without further purification. MS m/z=382.0 [M+H].

1. additionwere added
2. customThe mixture was capped with argon
3. customequipped with a reflux condenser
4. temperatureThe mixture was cooled to RT
5. filtrationthe resulting yellow precipitate was filtered
6. additionThe filtrate was diluted with water (200 mL) and saturated ammonium chloride (200 mL)
7. filtrationThe precipitate was filtered
8. customthe semisolid was triturated with water (˜200 mL)
9. customto provide a brown solid which
10. filtrationwas also filtered
11. washwashed with water
12. washThe combined solids were washed excessively with water
13. customdried overnight under a stream of air