tert-Butyl 2-(5-(2-methylpyridin-4-yl)-3-nitropyridin-2-yloxy)acetate → tert-Butyl 2-(3-amino-5-(2-methylpyridin-4-yl)pyridin-2-yloxy)acetate

HRID 1628323Notes

Reaction equation

HRID 1628323 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([N+:23]([O-])=O)[C:11]([O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1>[Pd]>[NH2:23][C:10]1[C:11]([O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:12][CH:13]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)[CH:9]=1

Participants

3

Reactant 1

HCID 69620969tert-Butyl 2-(5-(2-methylpyridin-4-yl)-3-nitropyridin-2-yloxy)acetate

Product 1

HCID 67497481tert-Butyl 2-(3-amino-5-(2-methylpyridin-4-yl)pyridin-2-yloxy)acetateYield 52.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a flask with 78.G (280 mg, 0.81 mmol) was added 112 mg 10% Pd/C. The reaction was purged with hydrogen and stirred under hydrogen for 4 hrs. After filtering through a pad of celite, silica gel purification afforded 78.H 134 mg (52%).

Workup

  1. customThe reaction was purged with hydrogen
  2. filtrationAfter filtering through a pad of celite, silica gel purification

Sources & evidence

ORD record
ord-76c5aeda742b444c8cc2c51f63810784
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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