Sodium Carbonate → HCID 56928551, compound

Temperature

100 °C

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was purged with nitrogen and charged with 103f (298 mg, 0.643 mmol), 112a (150 mg, 0.536 mmol), sodium carbonate (170 mg, 1.61 mmol), 1,4-dioxane (5 mL) and water (1 mL). This mixture was degassed with nitrogen for 30 min. Tetrakis(triphenylphosphine)palladium (62 mg, 0.054 mmol) was added. After heating at 100° C. for 3 h, the reaction mixture was cooled to room temperature and partitioned between water (40 mL) and methylene chloride (100 mL). The layers were separated, and the aqueous phase was extracted with methylene chloride (2×50 mL). The organic extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was dissolved in a mixture of methanol (5 mL), and potassium carbonate (500 mg, 3.62 mmol) was added. After stirring at room temperature for 2 h, the reaction mixture was partitioned between water (20 mL) and methylene chloride (20 mL). The layers were separated, and the aqueous phase was extracted with methylene chloride (2×20 mL). The organic extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to afford 112 in 27% yield (70 mg) as an off-white solid: mp 149-150° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.54 (s, 1H), 9.14 (d, 1H, J=2.0 Hz), 8.44 (m, 1H), 8.18 (dd, 1H, J=5.0, 1.5 Hz), 7.73-7.71 (m, 2H), 7.63-7.59 (m, 2H), 7.52 (t, 1H, J=8.0 Hz), 7.48 (s, 1H), 7.44 (dd, 1H, J=8.0, 1.5 Hz), 7.30 (dd, 1H, J=7.5, 4.5 Hz), 4.93 (s, 2H), 4.88 (t, 1H, J=5.0 Hz), 4.44 (d, 2H, J=5.0 Hz), 3.56 (s, 3H), 1.37 (s, 9H); MS (ESI+) m/z 496.2 (M+H).

1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
2. temperaturereflux condenser
3. customwas purged with nitrogen
4. customThis mixture was degassed with nitrogen for 30 min
5. temperaturethe reaction mixture was cooled to room temperature
6. custompartitioned between water (40 mL) and methylene chloride (100 mL)
7. customThe layers were separated
8. extractionthe aqueous phase was extracted with methylene chloride (2×50 mL)
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. additionwas added
13. customthe reaction mixture was partitioned between water (20 mL) and methylene chloride (20 mL)
14. customThe layers were separated
15. extractionthe aqueous phase was extracted with methylene chloride (2×20 mL)
16. dry with materialdried over sodium sulfate
17. filtrationfiltered
18. concentrationconcentrated under reduced pressure
19. customThe resulting residue was purified by flash chromatography

ORD record

ord-f96c7e95c7f64044adcc22e09ccdbb62

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249123B2