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

HRID 1847580Notes

Reaction equation

HRID 1847580 reaction equation
[C:1]([C:5]1[N:6]([CH2:19][CH2:20][OH:21])[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]>C(O)C.[Pd]>[NH2:16][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:19][CH2:20][OH:21])[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:13][C:12]=2[C:11]=1[C:14]#[N:15]

Participants

4

Reactant 1

HCID 581832442-tert-butyl-1-(2-hydroxyethyl)-5-nitro-1H-indole-4-carbonitrile

Product 1

HCID 581832225-amino-2-tert-butyl-1-(2-hydroxyethyl)-1H-indole-4-carbonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-tert-butyl-1-(2-hydroxyethyl)-5-nitro-1H-indole-4-carbonitrile (180 mg, 0.63 mmol) in ethanol (6 mL) under N2 atmosphere was added Pd—C (5% wt, 18 mg). The reaction was flushed with N2 (g) and then with H2 (g) and stirred under H2 (atm) at room temperature for 1.5 hours. The reaction was filtered over Celite and concentrated to yield the product (150 mg, 93%). ESI-MS m/z calc. 257.2, found 258.5 (M+1)+. Retention time 1.26 minutes.

Workup

  1. customThe reaction was flushed with N2 (g)
  2. filtrationThe reaction was filtered over Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e6986d8cebeb4c86a1a1eb096525fb04
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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