Hydrochloric Acid → HCID 68276030, compound

HRID 1475935Notes

Reaction equation

HRID 1475935 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:21]=[C:11]3[CH:12]=[C:13]([C:16]([O:18]CC)=[O:17])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.O.O[Li].O.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:21]=[C:11]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68276034Ethyl 2-(4-bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylate

Product 1

HCID 68276030HCID 68276030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(4-bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylate (2.40 g, 7.0 mmol) was dissolved in THF (50 mL) and water was added (12 mL) followed by LiOH—H2O (877 mg, 20.9 mmol). The mixture was stirred overnight at room temperature and 1M HCl (ca 28 mL) was added. The mixture was extracted with EtOAc (2×25 mL) and the combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford a crude white solid that was directly used into the next step. LCMS m/z 317.0, 319.0 (M+H)+, ret. time 2.62 min.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×25 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a crude white solid that

Sources & evidence

ORD record
ord-1432a248e6cc4feca1b483da4e1ae9c2
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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