3-(3-Tert-butyl-4-methoxy-5-nitrophenyl)-2-methoxypyridine → 3-Tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenylamine

HRID 2390819Notes

Reaction equation

HRID 2390819 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:8]=[C:9]([N+:13]([O-])=O)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO.[Pd]>[C:1]([C:5]1[C:10]([O:11][CH3:12])=[C:9]([NH2:13])[CH:8]=[C:7]([C:16]2[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 670700103-(3-Tert-butyl-4-methoxy-5-nitrophenyl)-2-methoxypyridine

Product 1

HCID 670698823-Tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

step 2—To a solution of 98 (0.98 g, 3.1 mmol) in EtOAc/MeOH (2:1, 30 mL) was added 10% Pd/C (0.10 g). A stream of hydrogen gas was bubbled through the solution for 20 min then the solution was stirred at RT for 16 h. The reaction mixture was filtered and concentrated to afford 3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenylamine (100).

Workup

  1. customA stream of hydrogen gas was bubbled through the solution for 20 min
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-336aa2602d794b458f3d8e414834a5a3
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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