Sodium Hydroxide → Pyrazolo[1,5-a]pyridin-5-ylmethanol

HRID 876816Notes

Reaction equation

HRID 876816 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[CH:10][C:11](C(OC)=O)=[C:5]2[CH:4]=1.[OH-].[Na+]>OS(O)(=O)=O>[N:9]1[N:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][C:5]2=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11030983HCID 11030983, compound

Product 1

HCID 11073571Pyrazolo[1,5-a]pyridin-5-ylmethanol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of methyl 5-(hydroxymethyl)pyrazolo[1,5-a]pyridine-3-carboxylate Y-6 (1.9 g, 9.1 mmol) in 40% H2SO4 was stirred at 80° C. for 24 h, then neutralized with 3N NaOH to pH=7-8. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford the title compound (1.1 g). MS (m/z): 149 (M+1)+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ff1292ebc44d48fcb46067e1e41cd5c7
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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