Sodium hydride → HCID 59287327, compound

HRID 2176849Notes

Reaction equation

HRID 2176849 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[H-].[Na+].[CH3:12][C:13]1[C:18]([CH3:19])=[C:17]([N+]([O-])=O)[CH:16]=[CH:15][N+:14]=1[O-:23]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:16]=[CH:15][N+:14]([O-:23])=[C:13]([CH3:12])[C:18]=2[CH3:19])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxideHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 59287327HCID 59287327, compoundYield 175.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a room temperature solution of 4-bromo-3-fluorophenol (15 g, 78.53 mmol) in DMF (50 ml) was added sodium hydride (3.32 g, 85.67 mmol, 60% in mineral oil) portionwise. After stirring for 10 minutes 2,3-dimethyl-4-nitro-pyridine 1-oxide (1.05 g, 6.28 mmol) was added The reaction mixture was heated at 180° C. for 60 minutes under microwave irradiation. After cooling to room temperature the mixture was filtered through a diatomaceous earth pad and the filtrate was then diluted with EtOAc and washed with water. The solution was then extracted with additional EtOAc (2×150 ml). The organic layer was dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM to DCM/MeOH up to 5% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 21 (3.44 g, 19%).

Workup

  1. additionwas added The reaction mixture
  2. temperatureAfter cooling to room temperature the mixture
  3. filtrationwas filtered through a diatomaceous earth pad
  4. additionthe filtrate was then diluted with EtOAc
  5. washwashed with water
  6. extractionThe solution was then extracted with additional EtOAc (2×150 ml)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customthe solvent evaporated in vacuo
  9. customThe crude product was purified by column chromatography (silica gel
  10. customThe desired fractions were collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-01ed3c7910e94c038feadd0092acfb89
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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