Water → HCID 21874975, compound

Temperature

80 °C

A solution of 1.09 g (4.67 mmol) of compound 260A in 20 mL AcOH with 10 mL EtOAc and 2 mL H2O was heated to 80° C. and treated with iron powder (1.3 g, 23.4 mmol). The mixture was heated at 80° C. for 40 min and then allowed to cool to rt. The mixture was filtered through Celite eluting with EtOAc. The filtrate was washed with sat. aq. NaHCO3, dried over MgSO4, and concentrated in vacuo. N,N-diethylaniline (10 mL) was added, and the reaction was heated at 215° C. for 6 h. After cooling to rt, 1 N aqueous. HCl (20 mL) was added, and the reaction was stirred at room temperature for 2 h. The mixture was extracted with EtOAc (3×30 mL). The organic phase was washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with 25% EtOAc in hexanes to give compound 260B (320 mg, 35%) as a beige solid.

1. temperatureto cool to rt
2. filtrationThe mixture was filtered through Celite
3. washeluting with EtOAc
4. washThe filtrate was washed with sat. aq. NaHCO3
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. additionN,N-diethylaniline (10 mL) was added
8. temperaturethe reaction was heated at 215° C. for 6 h
9. temperatureAfter cooling to rt
10. additionHCl (20 mL) was added
11. extractionThe mixture was extracted with EtOAc (3×30 mL)
12. washThe organic phase was washed with saturated aqueous NaHCO3
13. dry with materialdried over MgSO4
14. concentrationconcentrated in vacuo
15. customThe crude material was purified by flash column chromatography on silica gel eluting with 25% EtOAc in hexanes

ORD record

ord-e4a5d8306ee7494c8df304af49c8d146

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953679B2