2-Tert-butyl-6-fluoro-5-nitro-1H-indole → 2-(tert-Butyl)-6-fluoro-1h-indol-5-amine

HRID 1908401Notes

Reaction equation

HRID 1908401 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[C:9]([F:17])[CH:8]=2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH2:14])=[C:9]([F:17])[CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 534211862-Tert-butyl-6-fluoro-5-nitro-1H-indole

Product 1

HCID 591293662-(tert-Butyl)-6-fluoro-1h-indol-5-amineYield 39.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-tert-butyl-6-fluoro-5-nitro-1H-indole (1.5 g, 6.36 mmol) and Ni (0.5 g) in MeOH (20 mL) was stirred under H2 atmosphere (1 atm) at the room temperature for 3 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to dryness. The residue was recrystallized in ether to give 2-tert-butyl-6-fluoro-1H-indol-5-amine (520 mg, 38%). 1H-NMR (300 MHz, DMSO-d6) δ 10.46 (brs, 1H), 6.90 (d, J=8.7 Hz, 1H), 6.75 (d, J=9.0 Hz, 1H), 5.86 (s, 1H), 4.37 (brs, 2H), 1.29 (s, 9H); MS (ESI) m/e 206.6.

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-6eddae43e68046659069dde1e183239d
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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