HCID 86698878, compound → HCID 86698877, compound

HRID 1844511Notes

Reaction equation

HRID 1844511 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=1>[Pd].CCO>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:4][C:3]=2[O:2][CH3:1])=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 86698878HCID 86698878, compound

Product 1

HCID 86698877HCID 86698877, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of tert-butyl {3-methoxy-4-[(5-nitropyridin-2-yl)oxy]phenyl}methylcarbamate (4.80 g) and palladium on carbon (5% wt., 1.36 g) in EtOH (100 mL) was stirred at 40° C. for 2 hours under a hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/2 to 3/7) to afford the title compound (3.58 g) as a yellow oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/2 to 3/7)

Sources & evidence

ORD record
ord-b15575a52c384a1fbfad6c372302d2d0
Source dataset
uspto-grants-2015_02
Patent number
US08946437B2

Reaction notes

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