Water → HCID 61720969, compound

A mixture of Example 1D (22.5 g, 68.2 mmol), iron powder (19.0 g, 341 mmol), and ammonium chloride (7.30 g, 136 mmol) in tetrahydrofuran (117 mL), ethanol (117 mL), and water (39 mL) was refluxed at 100° C. for 2 hours. The mixture was cooled just below reflux, and filtered through Celite. The filter cake was washed with warm methanol (3×50 mL). The solution was concentrated under reduced pressure, neutralized to a pH of about 8 with saturated NaHCO3 (150 mL), and extracted with ethyl acetate (3×100 mL). The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered, concentrated, and purified by flash chromatography (silica gel, 0-15% ethyl acetatehexane gradient) to provide the title compound.

1. temperatureThe mixture was cooled just
2. temperaturebelow reflux
3. filtrationfiltered through Celite
4. washThe filter cake was washed with warm methanol (3×50 mL)
5. concentrationThe solution was concentrated under reduced pressure
6. extractionextracted with ethyl acetate (3×100 mL)
7. washThe combined organics were washed with saturated aqueous sodium chloride
8. dry with materialdried (anhydrous magnesium sulfate)
9. filtrationfiltered
10. concentrationconcentrated
11. custompurified by flash chromatography (silica gel, 0-15% ethyl acetatehexane gradient)

ORD record

ord-6c381fc25bd84c7b84e434702556f1a7

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428514B2