HCID 59332679, compound → 6-Fluoroindole

To a stirred suspension of (1E)-(4-fluoro-2-nitrophenyl)ethanal semicarbazone (27.0 g, 0.110 mol) in THF (750 mL) in a 1 L bomb was added Rh/C %; 3.5 g, 0.002 mol Rh) slurried in toluene and Fe(OAc)2 (2.9 g, 0.017 mol). The bomb was charged with H2 to 50 atm and stirred at room temperature for 2 days. The reaction mixture was filtered through celite, washing with MeOH (150 mL). The filtrate was concentrated to give a black oil that was partitioned between DCM (500 mL) and water (300 mL). The layers were separated and the aqueous fraction was extracted with DCM (2×200 mL). The combined organic extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and treated with flash silica to decolourise the solution. The mixture was filtered concentrated under reduced pressure, giving 12.9 g (87%) of the title compound.

1. additionThe bomb was charged with H2 to 50 atm
2. filtrationThe reaction mixture was filtered through celite
3. washwashing with MeOH (150 mL)
4. concentrationThe filtrate was concentrated
5. customto give a black oil that
6. customwas partitioned between DCM (500 mL) and water (300 mL)
7. customThe layers were separated
8. extractionthe aqueous fraction was extracted with DCM (2×200 mL)
9. washThe combined organic extracts were washed with brine (200 mL)
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated under reduced pressure
12. dissolutionThe residue was dissolved in DCM (100 mL)
13. additiontreated with flash silica
14. filtrationThe mixture was filtered
15. concentrationconcentrated under reduced pressure

ORD record

ord-3278bdc0ed274a66b05547ce4698724b

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372875B2