Sodium hydride → 2-(4-Bromo-pyrazolo[3,4-c]pyridin-1-yl)-ethanol

HRID 446919Notes

Reaction equation

HRID 446919 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[C:7]=1/[CH:8]=[N:9]/[NH:10][CH2:11][CH2:12][OH:13].[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[N:10]([CH2:11][CH2:12][OH:13])[N:9]=[CH:8][C:7]=12

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 576068362-[(2E)-2-[(3,5-dibromo-4-pyridinyl)methylidene]hydrazinyl]ethanol2×

Product 1

HCID 576067822-(4-Bromo-pyrazolo[3,4-c]pyridin-1-yl)-ethanolYield 108.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to GP2, 520 mg of 2-{N′-[1-(3,5-Dibromo-pyridin-4-yl)-meth-(E)-ylidene]-hydrazino}-ethanol (Intermediate 1.2, 1.61 mmol, 1 eq) were dissolved in 14 mL dry THF, treated at rt with 155 mg 50-60% sodium hydride (3.54 mmol, 2.2 eq) and subsequently refluxed for 90 min. The reaction mixture was quenched with water, extracted with ethyl acetate, the combined organic layers dried and concentrated in vacuo to yield 424 mg of a crude product, which was optionally further purified by trituration or flash column chromatography.

Workup

  1. temperaturesubsequently refluxed for 90 min
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customthe combined organic layers dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2adca0a3a5cb4710ac7e26ffa6d7722d
Source dataset
uspto-grants-2013_07
Patent number
US08481539B2

Reaction notes

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