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

HRID 1908432Notes

Reaction equation

HRID 1908432 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-a06cf67437b141158b2b861c8ff229a0
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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