Pyridine → HCID 86699867, compound

Temperature

0 °C

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 114g (240 mg, 0.633 mmol), pyridine (150 mg, 1.90 mmol) and methylene chloride (10 mL). The solution was cooled to 0° C., and acetyl chloride (75 mg, 0.950 mmol) was added. The cooling bath was then removed, and the reaction mixture was stirred at room temperature for 1 h. After this time, the reaction mixture was partitioned between water (5 mL) and methylene chloride (5 mL), and the layers were separated. The aqueous phase was extracted with methylene chloride (2×10 mL), and the combined organic extracts were washed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and brine (10 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to afford 114h in 86% yield (231 mg) as a white solid: mp 172-173° C.; 1H NMR (500 MHz, CDCl3) δ 7.63 (d, 1H, J=8.0 Hz), 7.34-7.21 (m, 2H), 6.87 (s, 1H), 5.21 (s, 2H), 4.64 (s, 2H), 2.05 (s, 3H), 1.42 (s, 9H).

1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
2. customwas purged with nitrogen
3. customThe cooling bath was then removed
4. customAfter this time, the reaction mixture was partitioned between water (5 mL) and methylene chloride (5 mL)
5. customthe layers were separated
6. extractionThe aqueous phase was extracted with methylene chloride (2×10 mL)
7. washthe combined organic extracts were washed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and brine (10 mL)
8. dry with materialThe organic extracts were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified by flash chromatography

ORD record

ord-77459251c7cb4aee97babf277ede6997

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249123B2