HCID 69658837, compound → HCID 21955926, compound

HRID 2212980Notes

Reaction equation

HRID 2212980 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[CH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[NH:10][CH:9]=1>CO.[Pd]>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[NH:10][CH:9]=1

Participants

4

Reactant 1

HCID 69658837HCID 69658837, compound

Product 1

HCID 21955926HCID 21955926, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(2-oxo-cyclopentylidenemethyl)-1H-indole-5-carbonitrile (800 mg, 3.39 mMol) in methanol (120 mL) was hydrogentated at atmospheric pressure for 16 h over 10% Pd/C catalyst (300 mg). The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (5% ethyl acetate/hexanes-80% ethyl acetate/hexanes) to give 3-(2-oxo-cyclopentylmethyl)-1H-indole-5-carbonitrile (140 mg, 18%). LCMS (4.6×50 mm XTERRA C-18 S5 column, 5 mL/min, 0–100% MeOH/H2O/0.1% TFA, 2 min gradient): Tr=1.51 min, m/e 261 (M+H+Na)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (5% ethyl acetate/hexanes-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-41838290cdd04ba399eebf6514900f9b
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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