Sodium Hydroxide → HCID 117844063, compound

HRID 2209248Notes

Reaction equation

HRID 2209248 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([N:16]=[CH:17][C:18]=2C(OC)=O)[CH:12]=[C:13]([Cl:15])[CH:14]=1)C1C=CC=CC=1.CC(O)=O.Br.[OH-].[Na+]>Br>[Cl:15][C:13]1[CH:14]=[C:9]([OH:8])[C:10]2[N:11]([N:16]=[CH:17][CH:18]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 117843167Methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 117844063HCID 117844063, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridine-3-carboxylate (152 mg, 0.480 mmol) was dissolved in HBr (48%, 2.0 mL) and the reaction was heated to 100° C. for 1.5 h. AcOH/HBr (1.0 mL) was added and the reaction was stirred overnight. The mixture was cooled to 0° C. and neutralized with 1M NaOH. The aqueous layer was extracted with dichloromethane (3×) and the combined organics were washed with brine, dried (MgSO4), filtered and concentrated to afford 6-chloropyrazolo[1,5-a]pyridin-4-ol.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (3×)
  2. washthe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4825887f532c4c3a8945b68d5096c86f
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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