HCID 57834728, compound → HCID 59129289, compound

HRID 1847723Notes

Reaction equation

HRID 1847723 reaction equation
[C:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57834728HCID 57834728, compound

Product 1

HCID 59129289HCID 59129289, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 1-tert-butyl-5-nitro-1H-indole (6.5 g, 0.030 mol) in MeOH (100 mL) was added Raney Nickel (0.65 g, 10%) under N2 protection. The mixture was stirred under hydrogen atmosphere (1 atm) at 30° C. for 1 h. The catalyst was filtered off and the filtrate was concentrated under vacuum to dryness. The residue was purified by column chromatography on silica gel (PE/EtOAc 1:2) to give 1-tert-butyl-1H-indol-5-amine (2.5 g, 45%). 1H-NMR (CDCl3, 400 MHz) δ 7.44 (d, J=8.8 Hz, 1H), 7.19 (dd, J=3.2 Hz, 1H), 6.96 (d, J=2.0 Hz, 1H), 6.66 (d, J=2.0, 8.8 Hz, 1H), 6.26 (d, J=3.2 Hz, 1H), 1.67 (s, 9H). MS (ESI) m/e (M+H+) 189.2.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under vacuum to dryness
  3. customThe residue was purified by column chromatography on silica gel (PE/EtOAc 1:2)

Sources & evidence

ORD record
ord-ce4f2f4573aa4af1bacef6d0a1fb130d
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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