6-Tert-butoxy-2-tert-butyl-5-nitro-1H-indole → 6-tert-butoxy-2-tert-butyl-1H-indol-5-amine

HRID 1991686Notes

Reaction equation

HRID 1991686 reaction equation
[C:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[NH:12]2)=[CH:8][C:7]=1[N+:19]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[NH:12]2)=[CH:8][C:7]=1[NH2:19])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 534216126-Tert-butoxy-2-tert-butyl-5-nitro-1H-indole

Product 1

HCID 591291526-tert-butoxy-2-tert-butyl-1H-indol-5-amineYield 32%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 6-tert-butoxy-2-tert-butyl-5-nitro-1H-indole (100 mg, 0.36 mmol) and Raney Ni (0.5 g) in MeOH (15 mL) was stirred under H2 atmosphere (1 atm) at the room temperature for 2.5 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to dryness. The residue was recrystallized in ether to give 6-tert-butoxy-2-tert-butyl-1H-indol-5-amine (30 mg, 32%). 1H-NMR (300 MHz, MeOD) 6.98 (s, 1H), 6.90 (s, 1H), 5.94 (d, J=0.6 Hz, 1H), 1.42 (s, 9H), 1.36 (s, 9H); MS (ESI) m/e 205.0.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure to dryness
  3. customThe residue was recrystallized in ether

Sources & evidence

ORD record
ord-2d4c69a5d0b74cecb052444e8e65464b
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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