Ethyl Acetate → HCID 43137983, compound

HRID 2232975Notes

Reaction equation

HRID 2232975 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.F[C:10]1N=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[C:18](OCC)(=O)C.C([O-])(O)=O.[Na+]>CN(C)C=O>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][C:14]2[CH:15]=[CH:16][CH:18]=[CH:10][C:11]=2[C:12]#[N:13])[CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27832543-Cyano-2-fluoropyridineHCID 667964713-Hydroxypyridine sodium salt

Product 1

HCID 43137983HCID 43137983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-hydoxypyridine sodium salt (purchased from Acros) (2.54 g, 26.71 mmol) in N,N-dimethyl formamide (50 mL) was added 2-fluoronicotinonitrile (3.32 g, 26.68 mmol) dropwise and the solution was heated at 100° C. for 2 hours. To the reaction mixture was added ethyl acetate (100 mL) and 1M NaHCO3 (150 mL) and it was filtered to remove black tar. The filtrate was decolorized with activated charcoal and extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The crude product was purified by flash column chromatography on silica gel using dichloromethane to give the title compound. MS (ESI+) m/z 197 (M+H)+.

Workup

  1. filtrationwas filtered
  2. customto remove black tar
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-0aef153fbbc041cb951a207c875707f3
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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