2-Amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile → 2-Amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile

HRID 2218245Notes

Reaction equation

HRID 2218245 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=2)[C:3]=1[C:4]#[N:5]>[Pd].C(OCC)(=O)C>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=2)[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 1

HCID 689535632-Amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile

Product 1

HCID 597696742-Amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-6-(2-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile (3.2 g, 7.2 mmol), 10% Pd—C (0.25 g) and ethyl acetate (1 L) was stirred at room temperature for 12 hrs. under a hydrogen atmosphere (2.5 atm). The reaction mixture was filtered on Celite Pad and the filtration was concentrated under reduced pressure to give starting compound 2, which was used for the next step without further purification (2.6 g, yield 87%).

Workup

  1. filtrationThe reaction mixture was filtered on Celite Pad
  2. filtrationthe filtration
  3. concentrationwas concentrated under reduced pressure
  4. customto give
  5. customwas used for the next step without further purification (2.6 g, yield 87%)

Sources & evidence

ORD record
ord-1a403d450baf4afab16480e576beb463
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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