Ethanol → HCID 70251217, compound

HRID 2202864Notes

Reaction equation

HRID 2202864 reaction equation
Br[CH:2]([CH3:6])[C:3](=O)[CH3:4].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][N:9]=1.CCO>O>[I:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([C:2]([CH3:6])=[C:3]([CH3:4])[N:7]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 131422-Butanone, 3-bromo-HCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 70251217HCID 70251217, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-bromobutan-2-one (1.0 g) and 2-amino-5-iodopyridine (800 mg) was added EtOH (25 ml), and the mixture was heated at 70° C. for 30 h. The reaction mixture was cooled, diluted with water, and extracted with DCM. The DCM layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (250 mg) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM
  3. washThe DCM layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-e31b3f59fe714d19bacb37e2f5ed3cd6
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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