HCID 44622906, compound → 3-tert-Butyl-1H-indol-5-amine

HRID 1403904Notes

Reaction equation

HRID 1403904 reaction equation
[C:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[NH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[NH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 44622906HCID 44622906, compound

Product 1

HCID 573569123-tert-Butyl-1H-indol-5-amineYield 19.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 3-tert-butyl-5-nitro-1H-indole (2.5 g, 11.6 mmol) in MeOH (30 mL) was added Raney Nickel (0.2 g) under N2 protection. The mixture was stirred under hydrogen atmosphere (1 atm) at 15° C. for 1 hr. The catalyst was filtered off and the filtrate was concentrated under vacuum to dryness. The residue was purified by preparative HLPC to afford 3-tert-butyl-1H-indol-5-amine (0.43 g, 19%). 1H NMR (CDCl3, 400 MHz) δ 7.72 (brs, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.0 Hz, 1H), 6.59 (dd, J=2.0, 8.4 Hz, 1H), 6.09 (d, J=1.6 Hz, 1H), 1.37 (s, 9H); MS (ESI) m/e (M+H+) 189.1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under vacuum to dryness
  3. customThe residue was purified by preparative HLPC

Sources & evidence

ORD record
ord-ec942d07a9a0499da3613f37e081736e
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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