[2-(6-nitro-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester → HCID 21071677, compound

HRID 2404656Notes

Reaction equation

HRID 2404656 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57567411[2-(6-nitro-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 21071677HCID 21071677, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of [2-(6-nitro-1H-indol-3-yl)-ethyl]carbamic acid tert-butyl ester (5 g, 16.4 mmol) and Raney Ni (1 g) in EtOH (100 mL) was stirred at room temperature under H2 (1 atm) for 5 h. Raney Ni was filtered off and the filtrate was evaporated under reduced pressure. The crude product was purified by column chromatography to give [2-(6-amino-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (B-10) (3 g, 67%). 1H NMR (DMSO-d6) δ 10.1 (br s, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.77-6.73 (m, 2H), 6.46 (d, J=1.5 Hz, 1H), 6.32 (dd, J=8.4, 2.1 Hz, 1H), 4.62 (s, 2H), 3.14-3.08 (m, 2H), 2.67-2.62 (m, 2H), 1.35 (s, 9H); ESI-MS 275.8 m/z (MH+).

Workup

  1. filtrationRaney Ni was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b95ce688ae2f4149b3bc6ea50d70d2ed
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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