Pyridine → HCID 66744781, compound

Temperature

-78 °C

To a cooled (−78° C.) clear, brown solution of 1E (2.63 g, 7.42 mmol) and pyridine (0.600 ml, 7.42 mmol) in dichloromethane (74.2 ml) was added dropwise over 30 min methyl chloroformate (0.516 ml, 6.68 mmol). The reaction was stirred at −78° C. After 1.5 h, the reaction was quenched with sat. NH4Cl and the reaction was allowed to warm to rt. The reaction was diluted with DCM and water and the layers were separated. The aqueous layer was extracted with DCM (1×). The combined organic layers were washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated. The residue dissolved in DCM (˜10 mL) and then hexane (˜300 mL) was added to give a brown suspension with brown gummy sticky substance at the bottom. The mixture was sonicated to give a mostly clear solution with the brown substance at the bottom. The solution decanted and the bottom substance rinsed with hexane, dried to give 1F (2.7 g, 88%) as a slightly brown foam. MS (ESI) m/z: 413.2 (M+H)+.

1. customthe reaction was quenched with sat. NH4Cl
2. temperatureto warm to rt
3. additionThe reaction was diluted with DCM and water
4. customthe layers were separated
5. extractionThe aqueous layer was extracted with DCM (1×)
6. washThe combined organic layers were washed with sat. NaHCO3, brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. dissolutionThe residue dissolved in DCM (˜10 mL)
11. additionhexane (˜300 mL) was added
12. customto give a brown suspension with brown gummy sticky substance at the bottom
13. customThe mixture was sonicated
14. customto give a mostly clear solution with the brown substance at the bottom
15. customThe solution decanted
16. washthe bottom substance rinsed with hexane
17. customdried

ORD record

ord-be9940883a1f447c89ca821fb14f8b68

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409908B2