7-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine → 7-bromo-N4-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)quinoline-3,4-diamine

HRID 549189Notes

Reaction equation

HRID 549189 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C@@H:16]([CH3:26])[CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>[Pt].C(#N)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C@@H:16]([CH3:26])[CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 671576277-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine

Product 1

HCID 691054407-bromo-N4-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)quinoline-3,4-diamineYield 88.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A 2-L, stainless-steel, Parr vessel was charged with platinum on carbon (5%, 4.0 g) and 10 mL of acetonitrile. A solution of 7-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine (40.5 g, 92.0 mmol) dissolved in 1 L of acetonitrile was then added. The reaction mixture was placed on Parr apparatus and shaken under H2 at 45 PSI (3.1×105 Pa) for 6 hours at ambient temperature. The reaction mixture was then filtered through a pad of CELITE filter agent. The pad rinsed with an additional 200 mL of acetonitrile and the combined filtrates were concentrated under reduced pressure to give 33.4 g 7-bromo-N4-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)quinoline-3,4-diamine as a yellow solid.

Workup

  1. additionwas then added
  2. filtrationThe reaction mixture was then filtered through a pad of CELITE
  3. filtrationfilter agent
  4. washThe pad rinsed with an additional 200 mL of acetonitrile
  5. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c57f61852b446f78aa7e441dce3bd71
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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