[3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid benzyl ester → 3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine

HRID 13712Notes

Reaction equation

HRID 13712 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][CH:17]=[C:16]2[C:20]1([CH2:30][CH3:31])[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:30]([C:20]1([C:16]2[C:15]3[C:19](=[C:11]([NH2:10])[CH:12]=[CH:13][CH:14]=3)[NH:18][CH:17]=2)[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)[CH3:31]

Participants

4

Reactant 1

HCID 58941681[3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid benzyl ester

Product 1

HCID 589417073-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamineYield 94.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of [3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid benzyl ester (7.78 g, 18.2 mmol) and 20% palladium hydroxide on carbon (1.6 g) in ethanol is hydrogenated at 50° C. at 60 psi for 18 hours. After filtration of the catalyst the solution is concentrated in vacuo to furnish the title compound as a black solid (5.04 g, 94%). LC-MS m/z 295.1 (M++1).

Workup

  1. filtrationAfter filtration of the catalyst the solution
  2. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-4537137c67e446c981d01e013eda5aba
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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