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

HRID 1908403Notes

Reaction equation

HRID 1908403 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-400127d54c7c4af48dc34af8e7aa63b8
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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