HCID 21050792, compound → HCID 69659045, compound

HRID 2212973Notes

Reaction equation

HRID 2212973 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:21])=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:21])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 21050792HCID 21050792, compound

Product 1

HCID 69659045HCID 69659045, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(3-cyano-1H-indol-5-yl)-cyclopent-1-enecarboxylic acid ethyl ester (0.97 g, 3.46 mMol) in methanol (50 mL) was treated with 10% palladium(0) on carbon (0.35 g) and hydrogenated at 50 psi in a Parr apparatus for 22 h. The mixture was filtered through Celite® 545 and concentrated in vacuo to give the product as a clear oil which solidified upon standing (0.95 g, 97%). 1H-NMR (500 MHz, CDCl3) δ 8.76 (1H, br s), 7.65 (1H, d, J=2.0 Hz), 7.60 (1H, s), 7.25 (1H, d, J=8.5 Hz), 7.18 (1H, m), 3.71 (2H, m), 3.57 (1H, m), 3.21 (1H, m), 2.16 (m, 4H), 2.02 (1H, m), 1.78 (1H, m), 0.85 (3H, t, J=7.0 Hz).

Workup

  1. filtrationThe mixture was filtered through Celite® 545
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38fb6ea1041a41e3b6157d1378d3a4e0
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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