HCID 39743078, compound → HCID 43448128, compound

HRID 930904Notes

Reaction equation

HRID 930904 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[N+:15]([O-])=O.[H][H]>O1CCCC1.[Pd]>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[NH2:15]

Participants

5

Reactant 2

HCID 39743078HCID 39743078, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 43448128HCID 43448128, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 252a (10.0 g, 30.4 mmol) in tetrahydrofuran (150 mL) was added to 10% Pd/C (1.616 g, 15.18 mmol) in a 250 mL bottle and the mixture was stirred for 24 hour under a 30 psi hydrogen atmosphere at 40° C. The mixture was filtered through a nylon membrane and concentrated. The residue was purified flash chromatography (silica gel, 70:30 ethyl acetate/hexanes) to provide the title compound (8.6 g, 55% yield).

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. customThe residue was purified flash chromatography (silica gel, 70:30 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bdf2232864054a0fb6c9ac35b21264b8
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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