5-{[Tert-butyl(dimethyl)silyl]ethynyl}-2-nitrothiophene-3-carboxamide → 2-Amino-5-{[tert-butyl(dimethyl)silyl]ethynyl}thiophene-3-carboxamide

HRID 386139Notes

Reaction equation

HRID 386139 reaction equation
[Si:1]([C:8]#[C:9][C:10]1[S:14][C:13]([N+:15]([O-])=O)=[C:12]([C:18]([NH2:20])=[O:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pt]>[NH2:15][C:13]1[S:14][C:10]([C:9]#[C:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:11][C:12]=1[C:18]([NH2:20])=[O:19]

Participants

4

Reactant 1

HCID 595263865-{[Tert-butyl(dimethyl)silyl]ethynyl}-2-nitrothiophene-3-carboxamide

Product 1

HCID 595263352-Amino-5-{[tert-butyl(dimethyl)silyl]ethynyl}thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

To 5-{[tert-butyl(dimethyl)silyl]ethynyl}-2-nitrothiophene-3-carboxamide (100 mg, 0.32 mmol) in MeOH (8.0 mL) was added 3% Pt/C doped with 0.6% V (21 mg, 3.2 μmol). The reaction was stirred under an H2 balloon at room temperature for 2 h. The solution was diluted with MeOH, filtered through Celite, combined with silica gel, and evaporated. Flash chromatography (dry load, 25-100% EtOAc/hexanes) afforded the title compound as a tan solid.

Workup

  1. filtrationfiltered through Celite
  2. customevaporated
  3. dry with materialFlash chromatography (dry load, 25-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-552c6d6edb5941918ae299007c3891de
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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