Potassium Carbonate → HCID 66994464, compound

HRID 335180Notes

Reaction equation

HRID 335180 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=1.F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>CN(C=O)C>[NH2:7][C:8]1[C:13]([O:14][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 66994464HCID 66994464, compoundYield 72.72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heated a mixture of potassium carbonate (31.38 g, 227.0 mmol), 2-aminopyridin-3-ol (10.00 g, 90.82 mmol), 4-fluorobenzonitrile (11.00 g, 90.82 mmol), and DMF (80 mL) at 90° C. for 3 hours. Cooled, partitioned between ethyl acetate and water, washed the organic layer twice with water, once with 2N NaOH, brine, dried, and concentrated. Dissolved the residue in dichloromethane (20 mL), added hexanes (150 mL), concentrated to 130 mL, filtered, and dried to afford the title compound (13.95 g, 72.72% yield) as a tan powder.

Workup

  1. temperatureHeated
  2. temperatureCooled
  3. custompartitioned between ethyl acetate and water
  4. washwashed the organic layer twice with water
  5. dry with materialonce with 2N NaOH, brine, dried
  6. concentrationconcentrated
  7. dissolutionDissolved the residue in dichloromethane (20 mL)
  8. additionadded hexanes (150 mL)
  9. concentrationconcentrated to 130 mL
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-ba527ef8d1db4d40b41dcfc55b791ebd
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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