4-Isopropylphenol → HCID 68280916, compound

HRID 1622586Notes

Reaction equation

HRID 1622586 reaction equation
Br[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].N1C=CC=CC=1C.[Cl-].[NH4+]>CS(C)=O.[Cu](I)I>[CH3:18][CH:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:22][CH:21]=1)[CH3:19]

Participants

8

Reactant 5

HCID 74654-IsopropylphenolHCID 79752-MethylpyridineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 68280916HCID 68280916, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromopyridin-2-amine (1200 mg), tripotassium phosphate (2945 mg), 4-isopropylphenol (1134 mg), copper iodide (I) (132 mg) and picoline acid (171 mg) in DMSO (40 mL) was stirred under a nitrogen atmosphere at 80° C. overnight. The reaction mixture was added to saturated aqueous ammonium chloride solution, filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (180.4 mg) as a pale-brown solid.

Workup

  1. filtrationfiltered through celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1937864eec80481f87e598b8cfc6ffc9
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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