Methanol → HCID 69224754, compound

HRID 2223230Notes

Reaction equation

HRID 2223230 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)=[CH:8]2)=[O:4].CO.C1COCC1>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)=[CH:8]2)=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 69222029HCID 69222029, compound

Product 1

HCID 69224754HCID 69224754, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

An oven dried 2L round bottom flask with magnetic stirbar under argon was charged with 2-(4-Nitro-phenyl)-1H-indole-5-carboxylic acid methyl ester (9.33 g, 31.52 mmol), methanol (600 mL), and THF (300 mL). The palladium catalyst (3.358, 10% wt, 3.152 mmol) was carefully added in portions then acetic acid (2 ml) was added. The mixture was evacuated then a balloon filled with H2 (g) was placed over the mixture. The reaction mixture was stirred at room temperature overnight. The mixture was filtered through a pad of celite. The celite pad was washed with ethyl acetate. The filtrate was concentrated to about 250 ml then filtered through a plug of silica gel and eluted with 70% Ethyl acetate:30% Hexanes then with ethyl acetate. The filtrate was concentrated and slurried in about 70 ml boiling methanol. The crude product was then purified on silica gel using 7:3 ethylacetate:hexanes as eluant to give 4.5 g of the pure product. Yield (4.5 g, 53.7%)

Workup

  1. dry with materialAn oven dried 2L round bottom flask with magnetic stirbar under argon
  2. customThe mixture was evacuated
  3. additiona balloon filled with H2 (g)
  4. filtrationThe mixture was filtered through a pad of celite
  5. washThe celite pad was washed with ethyl acetate
  6. concentrationThe filtrate was concentrated to about 250 ml
  7. filtrationthen filtered through a plug of silica gel
  8. washeluted with 70% Ethyl acetate
  9. concentrationThe filtrate was concentrated
  10. customThe crude product was then purified on silica gel using 7:3 ethylacetate

Sources & evidence

ORD record
ord-1bde8912279f4c07b7c1b1af2900bc07
Source dataset
uspto-grants-2008_05
Patent number
US07375118B2

Reaction notes

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