Potassium Carbonate → HCID 11482333, compound

HRID 1749120Notes

Reaction equation

HRID 1749120 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:23]([OH:26])[CH2:24][CH3:25]>C(#N)C>[CH2:1]([O:8][C:9]1[C:10](=[O:15])[N:11]([CH2:25][CH2:24][CH2:23][OH:26])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156664523-(Benzyloxy)pyridin-2-olHCID 21966311HCID 21966311, compound

Product 1

HCID 11482333HCID 11482333, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To the solution of Compound 6 (0.202 g, 1 mmol) in acetonitrile was added K2CO3 (2 equiv.) followed by iodopropanol (0.186 g, 1 mmol). The reaction mixture was stirred at 65° C. overnight. On completion of the reaction, the reaction mixture was filtered and solvent was evaporated under vacuum. The residue was dissolved in water and extracted three times with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuum. The resulting compound 12 was purified by column chromatography (2:100, CH3OH/CH2Cl2). Yield: (85%)

Workup

  1. customOn completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. customsolvent was evaporated under vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted three times with CH2Cl2
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customThe resulting compound 12 was purified by column chromatography (2:100, CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ca06dbb9fe5f41d3bf2557ee7d4d832a
Source dataset
uspto-grants-2015_10
Patent number
US09156772B2

Reaction notes

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