Dimethylformamide → Tert-butyl {4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate

HRID 1800410Notes

Reaction equation

HRID 1800410 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([OH:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[N:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][C:18]2[CH:23]=[N:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 44668374tert-butyl N-(3-hydroxy-4-methylphenyl)carbamate

Product 1

HCID 57749145Tert-butyl {4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}carbamateYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl(3-hydroxy-4-methylphenyl)carbamate (3.14 g, 14.1 mmol), 5-bromo-2-nitropyridine (2.38 g, 11.7 mmol), cesium carbonate (5.72 g, 17.6 mmol) and N,N-dimethylformamide (25 mL) was stirred at room temperature for 15 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (basic silica gel, hexane/ethyl acetate=80/20→0/100) to give the title compound (1.86 g, 44%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (basic silica gel, hexane/ethyl acetate=80/20→0/100)

Sources & evidence

ORD record
ord-54012ae9a605452185af60faf57debb5
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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