5-tert-butyl-6-nitro-1H-indole → HCID 57470208, compound

HRID 73954Notes

Reaction equation

HRID 73954 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH2:14])[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 574702075-tert-butyl-6-nitro-1H-indole

Product 1

HCID 57470208HCID 57470208, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Raney Ni (3 g) was added to 5-tert-butyl-6-nitro-1H-indole (14.7 g, 67 mmol) in methanol (100 mL). The mixture was stirred under hydrogen (1 atm) at 30° C. for 3 h. The catalyst was filtered off. The filtrate was dried over Na2SO4 and concentrated. The crude dark brown viscous oil was purified by column chromatography (10-20% EtOAc/petroleum ether) to give 5-tert-butyl-1H-indol-6-ylamine (B-24) as a gray solid (11 g, 87%). 1H NMR (300 MHz, DMSO-d6) δ 10.3 (br s, 1H), 7.2 (s, 1H), 6.9 (m, 1H), 6.6 (s, 1H), 6.1 (m, 1H), 4.4 (br s, 2H), 1.3 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. dry with materialThe filtrate was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude dark brown viscous oil was purified by column chromatography (10-20% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-2e778528986a4dd0a928b8a36038a39a
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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