Sodium hydride → 4-Bromo-1-methyl-1H-pyrazolo(3,4-c)pyridine

HRID 446918Notes

Reaction equation

HRID 446918 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][CH3:11].[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[N:10]([CH3:11])[N:9]=[CH:8][C:7]=12

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 576067973,5-Dibromoisonicotinaldehyde methylhydrazone2×

Product 1

HCID 576069364-Bromo-1-methyl-1H-pyrazolo(3,4-c)pyridineYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to GP 2, 5.34 g of N-[1-(3,5-Dibromo-pyridin-4-yl)-meth-(E)-ylidene]-N′-methyl-hydrazine (Intermediate 1.1, 18.23 mmol, 1 eq) were dissolved in 163 mL dry THF, treated at rt with 994 mg 50-60% sodium hydride (22.78 mmol, 1.2 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. The precipitate was filtered and subsequently triturated with diisopropylether to yield 1.71 g of the desired product. Flash column chromatography of the mother liquor provided a second batch of the analytically pure product.

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
  6. filtrationThe precipitate was filtered
  7. customsubsequently triturated with diisopropylether

Sources & evidence

ORD record
ord-79367e01fe9a40ce8215f32a3aacd70a
Source dataset
uspto-grants-2013_07
Patent number
US08481539B2

Reaction notes

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