Triethylsilane → HCID 117843806, compound

HRID 2209241Notes

Reaction equation

HRID 2209241 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([N:16]=[CH:17][C:18]=2[CH2:19]O)[CH:12]=[C:13]([Cl:15])[CH:14]=1)C1C=CC=CC=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Cl:15][C:13]1[CH:14]=[C:9]([OH:8])[C:10]2[N:11]([N:16]=[CH:17][C:18]=2[CH3:19])[CH:12]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 117843305(4-(Benzyloxy)-6-chloropyrazolo[1,5-a]pyridin-3-yl)methanol

Product 1

HCID 117843806HCID 117843806, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridin-3-yl)methanol (274 mg, 0.946 mmol) in TFA (3.0 mL) was added triethylsilane (0.604 mL, 3.78 mmol). The reaction was stirred at 60° C. overnight. Incomplete removal of the benzyl group was observed. The reaction was concentrated, dissolved in HBr (48%, 3.5 ml) and the reaction was heated at 100° C. overnight. The reaction was cooled and neutralized by the addition of 2N NaOH. The aqueous layer was extracted with EtOAc (3×) and the combined organics were washed with saturated NaHCO3 (aq), brine, dried (MgSO4), filtered and concentrated to provide 6-chloro-3-methylpyrazolo[1,5-a]pyridin-4-ol. LCMS-ES I+(m/z): [M+H]+ calcd for C8H7ClN2O: 183.0; found 183.0.

Workup

  1. customIncomplete removal of the benzyl group
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in HBr (48%, 3.5 ml)
  4. temperaturethe reaction was heated at 100° C. overnight
  5. temperatureThe reaction was cooled
  6. additionneutralized by the addition of 2N NaOH
  7. extractionThe aqueous layer was extracted with EtOAc (3×)
  8. washthe combined organics were washed with saturated NaHCO3 (aq), brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-153ae256731e41b49cbcb1977ce9743d
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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