HCID 54394719, compound → HCID 19769824, compound

HRID 1590466Notes

Reaction equation

HRID 1590466 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][CH2:10][C:9](=[CH:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[C:8](=[O:22])[C:7]2=1.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[C:8](=[O:22])[C:7]2=1

Participants

5

Reactant 2

HCID 54394719HCID 54394719, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19769824HCID 19769824, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

8-Fluoro-1,2,3,9-tetrahydro-3-[(5-methyl-1H-imidazol-4-yl) methylene]-4H-carbazol-4-one (728 mg) in absolute ethanol (30 ml) was added to a suspension of 5% palladium on charcoal (100 mg) in ethanol (30 ml), and the resulting mixture was hydrogenated at room temperature and atmospheric pressure until hydrogen uptake had ceased. The mixture was filtered, and the filtrate was evaporated in vacuo to leave an oil which was purified by FCC eluting with ethanol:ethyl acetate (1:5) to give the title compound (342 mg), m.p. 135°-140°, t.l.c. (ethanol:ethyl acetate, 1:5) Rf 0.175.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customto leave an oil which
  5. customwas purified by FCC
  6. washeluting with ethanol:ethyl acetate (1:5)

Sources & evidence

ORD record
ord-374b447bea57495eb1f2b86c36900ac5
Source dataset
uspto-grants-1993_04
Patent number
US05202343

Reaction notes

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