3-(5-{2-[Benzyl-(2-methoxyethyl)-amino]-ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone → 3-(5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone

HRID 1007637Notes

Reaction equation

HRID 1007637 reaction equation
C([N:8]([CH2:32][CH2:33][O:34][CH3:35])[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]1[C:22](=[O:31])[NH:23][C:24]3[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:15]2)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH3:35][O:34][CH2:33][CH2:32][NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]1[C:22](=[O:31])[NH:23][C:24]3[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:15]2

Participants

4

Reactant 1

HCID 102052713-(5-{2-[Benzyl-(2-methoxyethyl)-amino]-ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone

Product 1

HCID 99077363-(5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd/C (840 mg) was added to a solution (150 mL) of 3-(5-{2-[Benzyl-(2-methoxyethyl)-amino]-ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone, Compound 1-27, (840 mg, 1.8 mmol) in EtOAc (150 mL), and the resulting mixture was stirred under a hydrogen balloon for 18 h. The catalyst was removed by filtration and the filtrate concentrated to a yellow solid which was purified by chromatography on a silica column. Elution with EtOAc to 25% NH3-EtOH/EtOAc gave 3-(5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone (2-1) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 11.05 (s, 1H), 9.65 (br s, 1H), 8.32 (s, 1H), 7.67 (d, 1H, J=8 Hz), 7.51 (t, 1H, J=8 Hz), 7.34 (d, 1H, J=8 Hz), 7.29 (t, 1H, J=8 Hz), 7.24 (d, 1H, J=8 Hz), 7.09 (s, 1H), 6.96 (s, 1H), 6.90 (dd, 1H, J=8, 2 Hz), 4.15 (t, 2H, J=5 Hz), 3.55 (t, 2H, J=5 Hz), 3.38 (s, 3H), 3.07 (t, 2H, J=5 Hz), 2.91 (t, 2H, J=5 Hz).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated to a yellow solid which
  3. customwas purified by chromatography on a silica column
  4. washElution with EtOAc to 25% NH3-EtOH/EtOAc

Sources & evidence

ORD record
ord-b0528f8d37d14305b7919118ebebfe96
Source dataset
uspto-grants-2004_09
Patent number
US06794393B1

Reaction notes

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