2-Naphthol → HCID 55374169, compound

HRID 1818006Notes

Reaction equation

HRID 1818006 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13].[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18]>CN(C=O)C.O>[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([O:13][C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:3]=2)[C:16]=1[C:17]#[N:18]

Participants

6

Reactant 3

HCID 86632-NaphtholHCID 24758Sodium hydrideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 55374169HCID 55374169, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a 20 mL vial containing a magnetic stir bar was added sodium hydride (103.7 mg, 4.32 mmol, 60% in mineral oil) followed by anhydrous DMF (2 mL) resulting in gas evolution. To this stirring reaction mixture was added 2-naphthol (623 mg, 4.32 mmol) as a solid in small portions over 5 min. The mixture was stirred at room temperature for 3 min and then 2,6-difluorobenzonitrile (601 mg, 4.32 mmol) in anhydrous DMF was added in one portion. The reaction mixture was heated in an oil bath at 100° C. for a total of 2 h and allowed to cool to room temperature. The reaction mixture was diluted with water (15 mL) and the resulting mixture was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (3×20 mL), dried (Na2SO4), filtered and concentrated to give I-189 as brown solid (1.216 g) of sufficient purity (contains 2-naphthol) to be used in the subsequent step. 1H NMR.

Workup

  1. additionTo a 20 mL vial containing a magnetic stir bar
  2. customresulting in gas evolution
  3. customTo this stirring reaction mixture
  4. temperatureThe reaction mixture was heated in an oil bath at 100° C. for a total of 2 h
  5. temperatureto cool to room temperature
  6. extractionthe resulting mixture was extracted with EtOAc (2×20 mL)
  7. washThe combined organic extracts were washed with water (3×20 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d19a009dcfc0490e8324da78fd0ff4b0
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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