2-tert-butyl-5-nitro-1H-indole-4-carbonitrile → 5-amino-2-tert-butyl-1H-indole-4-carbonitrile

HRID 1964456Notes

Reaction equation

HRID 1964456 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[CH:8]=[CH:9][C:10]([N+:16]([O-])=O)=[C:11]([C:14]#[N:15])[C:12]=2[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Ni]>[NH2:16][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:13][C:12]=2[C:11]=1[C:14]#[N:15]

Participants

4

Reactant 1

HCID 591295222-tert-butyl-5-nitro-1H-indole-4-carbonitrile

Product 1

HCID 591295115-amino-2-tert-butyl-1H-indole-4-carbonitrileYield 51%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-tert-butyl-5-nitro-1H-indole-4-carbonitrile (550 mg, 2.3 mmol) in EtOAc (10 mL) was added Raney Ni (0.1 g) under a nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature for 1 h. The catalyst was filtered over Celite and the filtrate was evaporated in vacuo to afford 5-amino-2-tert -butyl-1H-indole-4-carbonitrile (250 mg, 51%). 1H NMR (DMSO, 300 MHz) δ 10.93 (br s, 1 H), 7.25 (d, J=8.7 Hz, 1 H), 6.49 (d, J=8.7 Hz, 1 H), 5.94 (d, J=2.1 Hz, 1 H), 5.40 (br s, 2 H), 1.30 (s, 9 H). MS (ESI) m/z: 214.0 [M+H+].

Workup

  1. filtrationThe catalyst was filtered over Celite
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4ce6af0af5e84ff3b7c66b83dde29f86
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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