HCID 86642127, compound → HCID 66636723, compound

To a solution of (±)-diethyl 2,2′-(3-methyl-4-nitro-2-thioxo-2,3-dihydro-1H-indole-1,3-diyl)diacetate from Step C (900 mg, 6.31 mmol) in THF (40 mL) was added activated Raney nickel (ca. 4 g) and the reaction mixture was stirred at ambient temperature for 10 min. The reaction mixture was filtered through a pad of Celite, washing with THF. EtOAc (100 mL) was added to the filtrate and the mixture was concentrated under reduced pressure to a volume of about 100 mL. This mixture was diluted with EtOAc (300 mL) and washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=321 (M+1).

1. filtrationThe reaction mixture was filtered through a pad of Celite
2. washwashing with THF
3. additionEtOAc (100 mL) was added to the filtrate
4. concentrationthe mixture was concentrated under reduced pressure to a volume of about 100 mL
5. additionThis mixture was diluted with EtOAc (300 mL)
6. washwashed with saturated aqueous NaHCO3 (100 mL), brine (100 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by silica gel chromatography
11. washeluting with a gradient of hexane

ORD record

ord-6bc2e3d0e30e459f9d8463fa4852ef9a

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696192B2