2-tert-Butyl-1-methyl-5-nitro-1H-indole → 2-(1,1-Dimethylethyl)-1-methyl-1H-indol-5-amine

HRID 468327Notes

Reaction equation

HRID 468327 reaction equation
[C:1]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[N:6]([CH3:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 534211822-tert-Butyl-1-methyl-5-nitro-1H-indole

Product 1

HCID 591293302-(1,1-Dimethylethyl)-1-methyl-1H-indol-5-amineYield 66%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-1-methyl-5-nitro-1H-indole (3.00 g, 13.7 mmol) in MeOH (30 mL) was added Raney Ni (0.3 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The mixture was filtered through a Celite pad and the filtrate was evaporated under vacuum. The crude residue was purified by column chromatography on silica gel (P.E/EtOAc 20:1) to give 2-tert-butyl-1-methyl-1H-indol-5-amine (1.7 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.09 (d, J=8.4 Hz, 1H), 6.89-6.9 (m, 1H), 6.66 (dd, J=2.4, 8.7 Hz, 1H), 6.14 (d, J=0.6 Hz, 1H), 3.83 (s, 3H), 3.40 (brs, 2H), 1.45 (s, 9H); MS (ESI) m/e (M+H+) 203.1.

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe crude residue was purified by column chromatography on silica gel (P.E/EtOAc 20:1)

Sources & evidence

ORD record
ord-301807fb7bbc4d879d04d731087f0b4c
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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