HCID 68296657, compound → HCID 68296622, compound

HRID 1619452Notes

Reaction equation

HRID 1619452 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-])=O)=[CH:10][C:9]=2[CH3:18])=[O:5])[CH3:2].[H][H]>O1CCCC1.CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH2:15])=[CH:10][C:9]=2[CH3:18])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 68296657HCID 68296657, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68296622HCID 68296622, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 5 g 7-methyl-5-nitro-1H-indole-2-carboxylic acid ethyl ester and 0.5 g Pd/C 10% in 200 ml tetrahydrofuran/methanol (3:1) was stirred for 5 h under a pressure of 3 bar of hydrogen. The catalyst was filtered and the mixture was evaporated under reduced pressure. The residue was purified by silica gel chromatography (SiO2; cyclohexane/ethyl acetate 75:25→50:50).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe mixture was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (SiO2; cyclohexane/ethyl acetate 75:25→50:50)

Sources & evidence

ORD record
ord-345a9ec1d3244ddc8c89cea92d093ab0
Source dataset
uspto-grants-2014_07
Patent number
US08772305B2

Reaction notes

Loading…