3-(4-Chlorophenyl)-2-isopropyl-9-methyl-4-oxo-4H-pyrano[2,3-e]indole-7-carboxylic acid benzyl ester → HCID 68702222, compound

HRID 14480Notes

Reaction equation

HRID 14480 reaction equation
C(OC([N:11]1[C:19]2[C:14](=[C:15]3[O:23][C:22]([CH:24]([CH3:26])[CH3:25])=[C:21]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[C:20](=[O:34])[C:16]3=[CH:17][CH:18]=2)[C:13]([CH3:35])=[CH:12]1)=O)C1C=CC=CC=1>O1CCCC1.C(O)C.Cl.[Pd]>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:21]2[C:20](=[O:34])[C:16]3[C:15]([O:23][C:22]=2[CH:24]([CH3:25])[CH3:26])=[C:14]2[C:19](=[CH:18][CH:17]=3)[NH:11][CH:12]=[C:13]2[CH3:35])=[CH:32][CH:31]=1

Participants

6

Reactant 1

HCID 687002863-(4-Chlorophenyl)-2-isopropyl-9-methyl-4-oxo-4H-pyrano[2,3-e]indole-7-carboxylic acid benzyl ester

Product 1

HCID 68702222HCID 68702222, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 3-(4-chlorophenyl)-2-isopropyl-9-methyl-4-oxo-4H-pyrano[2,3-e]indole-7-carboxylic acid benzyl ester and its positional isomer (0.063 g, 0.13 mmol) and 20% Pd on activated carbon (0.013 g) in tetrahydrofuran (1.5 ml), ethanol (1.5 ml) and 5M HCl solution (0.75 ml) is stirred under a hydrogen atmosphere for 3.5 h at room temperature. The catalyst is removed by filtration through Celite filter aid, and the pad of Celite is washed with ethyl acetate and methylene chloride. The combined filtrates are evaporated in vacuo, and the residue is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 5:1) to afford the title compound as a pale orange solid.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. filtrationfilter aid
  3. washthe pad of Celite is washed with ethyl acetate and methylene chloride
  4. customThe combined filtrates are evaporated in vacuo
  5. customthe residue is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 5:1)

Sources & evidence

ORD record
ord-6751c4eadf9d473d9245d8a400a12fdc
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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