Hydrochloric Acid → HCID 118378998, compound

HRID 931025Notes

Reaction equation

HRID 931025 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:4]2[CH:3]=1.[I:14]I.Cl>C1COCC1>[I:14][C:6]1[N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 807IodineHCID 197709515-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid

Product 1

HCID 118378998HCID 118378998, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid (2.11 g) in THF (40 mL) was added 1M lithiumhexadisilazide THF solution (35.9 mL) at 0° C., the mixture was stirred for 30 min, and iodine (3.65 g) was added thereto. The reaction mixture was stirred overnight at room temperature under nitrogen gas atmosphere, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium thiosulfate solution, water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane/IPE to give the title compound (3.42 g).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature under nitrogen gas atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with aqueous sodium thiosulfate solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe residue was washed with hexane/IPE

Sources & evidence

ORD record
ord-bd828f6535c14c91a9506dd3c4502814
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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