Sodium hydride → HCID 53374913, compound

HRID 1405998Notes

Reaction equation

HRID 1405998 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[N:17][OH:18])[C:10]2[C:15](F)=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[O:18][N:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178526355HCID 178526355, compound

Product 1

HCID 53374913HCID 53374913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-(3-chlorophenyl)-3-fluoro-N′-hydroxypicolinimidamide, 3, (7.73 mmol) in DMF (50 mL) was added at 0° C. to a mixture of NaH (1.2 g, 31 mmol, 60% oil dispersion) in DMF (20 mL). After addition was complete, the ice bath was removed. An additional 12 h passed and the r×n was added to EtOAc:H2CO (1:1). The organic layer was separated and washed with H2CO, brine, dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the residue was purified by reverse phase liquid column chromatography (50-75% acetonitrile: water with 0.1% trifluoroacetic acid) to yield N-(3-chlorophenyl)isoxazolo[4,5-b]pyridin-3-amine as a pale yellow solid (0.52 g, 24% over two steps).

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. customAn additional 12 h
  4. additionthe r×n was added to EtOAc:H2CO (1:1)
  5. customThe organic layer was separated
  6. washwashed with H2CO, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by reverse phase liquid column chromatography (50-75% acetonitrile: water with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-83f1ed8259804e31bf267ed5ddd803e5
Source dataset
uspto-grants-2014_12
Patent number
US08916584B2

Reaction notes

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