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 1991881Notes

Reaction equation

HRID 1991881 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-d465cb3949ce413ba09c069a01da885c
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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