2-tert-Butyl-7-fluoro-5-nitro-1H-indole → 2-(Tert-butyl)-7-fluoro-1h-indol-5-amine

HRID 468347Notes

Reaction equation

HRID 468347 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)=[CH:9][C:8]=2[F:17])([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])=[CH:9][C:8]=2[F:17])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 534211892-tert-Butyl-7-fluoro-5-nitro-1H-indole

Product 1

HCID 513582832-(Tert-butyl)-7-fluoro-1h-indol-5-amineYield 31.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-7-fluoro-5-nitro-1H-indole (2.0 g, 8.5 mmol) in MeOH (20 mL) was added Ni (0.3 g) under nitrogen atmosphere. The reaction mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off through the celite pad and the filtrate was evaporated under vacuum. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 100:1) to give 2-tert-butyl-7-fluoro-1H-indol-5-amine (550 mg, 24%). 1H NMR (300 MHz, CDCl3) δ 7.87 (brs, 1H), 6.64 (d, J=1.5 Hz, 1H), 6.37 (dd, J=1.8, 12.3 Hz, 1H), 6.11 (dd, J=2.4, 3.6 Hz, 1H), 1.39 (s, 9H). MS (ESI) m/z (M+H+) 207.

Workup

  1. filtrationThe catalyst was filtered off through the celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 100:1)

Sources & evidence

ORD record
ord-004483e9702c43c8a06e99a7e0c60600
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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