Methanol → HCID 58437256, compound

HRID 1258223Notes

Reaction equation

HRID 1258223 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22]CC4C=CC=CC=4)=[O:21])=[CH:17][CH:18]=3)[C:13]([C:30]#[N:31])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].CO>[C].[Pd].O1CCCC1>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=3)[C:13]([C:30]#[N:31])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 58437437HCID 58437437, compound

Product 1

HCID 58437256HCID 58437256, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-cyano-5-benzyloxycarbonylindol-1-yl)benzoic acid ethyl ester (0.16 g) in a mixed solvent of methanol (5 mL) and tetrahydrofuran (5 mL) was added palladium-carbon powder (0.03 g) at 0° C. under an argon atmosphere, and this mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (0.057 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9952b20691cf42de9c9303df3e377984
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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