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

HRID 503313Notes

Reaction equation

HRID 503313 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-65dba9012157466b82afae136ba95f9f
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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