2-Bromopyridine → HCID 70116313, compound

HRID 467705Notes

Reaction equation

HRID 467705 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][NH:7][N:6]=1)=[O:4].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu-]=O>[CH3:1][N:2]([CH3:13])[C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 178484500HCID 178484500, compound

Product 1

HCID 70116313HCID 70116313, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4-nitro-1H-pyrazole-3-carboxylic acid dimethylamide (250 mg, 1.36 mmol) in DMF (5 ml) was flushed with argon. 2-Bromopyridine (0.17 ml, 1.76 mmol), ferric acetylacetone (144 mg, 0.4 mmol), copper(I)oxide (20 mg, 0.14 mmol) and cesium carbonate (885 mg, 2.7 mmol) were added consecutively and the reaction mixture was stirred at 110° C. overnight. After cooling down, the reaction mixture was partitioned between ethyl acetate (30 ml) and water (15 ml) and extracted. The organic layer was washed with brine, dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (102 mg, 29%).

Workup

  1. temperatureAfter cooling down
  2. customthe reaction mixture was partitioned between ethyl acetate (30 ml) and water (15 ml)
  3. extractionextracted
  4. washThe organic layer was washed with brine
  5. customdried
  6. customthe solvent was evaporated
  7. customThe product was obtained
  8. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-b6dab6091c514e179cf7fd99f781231f
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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