2-(Ethyl-{5-[1-(4-ethynyl-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-amino)-ethanol → 2-(Ethyl-{5-[1-(4-ethyl-phenyl)-1H-indol-5-yl]-pentyl}-amino)-ethanol

HRID 1633668Notes

Reaction equation

HRID 1633668 reaction equation
[CH2:1]([N:3]([CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1)[CH:16]=[CH:15]2)[CH2:4][CH2:5][OH:6])[CH3:2]>CO.[Pd]>[CH2:1]([N:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH3:28])=[CH:23][CH:22]=1)[CH:16]=[CH:15]2)[CH2:4][CH2:5][OH:6])[CH3:2]

Participants

4

Reactant 1

HCID 186794672-(Ethyl-{5-[1-(4-ethynyl-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-amino)-ethanol

Product 1

HCID 186794662-(Ethyl-{5-[1-(4-ethyl-phenyl)-1H-indol-5-yl]-pentyl}-amino)-ethanolYield 13.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

60 mg (0.16 mmol) 2-(Ethyl-{5-[1-(4-ethynyl-phenyl)-1H-indol-5-yl]-pent-4-ynyl}-amino)-ethanol in 10 ml MeOH were hydrogenated in the presence of 20 mg Pd/C, filtered and concentrated. Purification by column chromatography on silica gel with CH2Cl2/MeOH 9:1 yielded 8.0 mg 2-(Ethyl-{5-[1-(4-ethyl-phenyl)-1H-indol-5-yl]-pentyl}-amino)-ethanol as colorless oil, MS: 379 (MH+).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification by column chromatography on silica gel with CH2Cl2/MeOH 9:1

Sources & evidence

ORD record
ord-a59a4b9063ea42ea9a284ed235f8f68e
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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