HCID 70093703, compound → HCID 11057421, compound

HRID 635377Notes

Reaction equation

HRID 635377 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:18])[CH3:2]

Participants

4

Reactant 1

HCID 70093703HCID 70093703, compound

Product 1

HCID 11057421HCID 11057421, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

3-[1-(Benzenesulphonyl)-1H-indol-4-yl]acrylic acid ethyl ester (2.48 g, 6.98 mmol) was hydrogenated over 10% Pd-C (500 mg) in ethyl acetate-ethanol (4:1; 75 ml), under an atmosphere of hydrogen. The catalyst was removed by filtration after 4 h, and the solvents were removed to obtain the title compound as a colourless oil which crystallised on standing (2.47 g, 100%); δH (CDCl3, 360 MHZ) 1.10 (3H, t, J=6.8 Hz), 2.57 (2H, t, J=7.5 Hz), 3.06 (2H, t, J=7.5 Hz), 4.02 (2H, q, J=7.2 Hz), 6.66 (1H, d, J=0.72 Hz), 6.98 (1H, d, J=7.5 Hz), 7.14-7.18 (1H, m), 7.34-7.38 (2H, m), 7.43-7.48 (1H, m), 7.50 (1H, d, J=3.9 Hz), 7.77-7.82 (3H, m).

Workup

  1. customThe catalyst was removed by filtration after 4 h
  2. customthe solvents were removed

Sources & evidence

ORD record
ord-fc4049329575488ea1f0479816bef95c
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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