Acetic Acid → HCID 178434433, compound

HRID 1880395Notes

Reaction equation

HRID 1880395 reaction equation
[Br:1][CH:2]([CH:5]=O)[CH:3]=O.C[N:8]1[C:12]([NH2:13])=[CH:11][CH:10]=[N:9]1.[C:14](O)(=O)C>>[Br:1][C:2]1[CH:5]=[C:11]2[C:10]([CH3:14])=[N:9][NH:8][C:12]2=[N:13][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 749452-BromopropanedialHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 178434433HCID 178434433, compoundYield 9%

Procedure

A solution of 2-bromomalonaldehyde (4.0 g, 30 mmol) and methyl-1H-pyrazol-5-amine (2.57 g, 26.5 mmol) in acetic acid (40 mL) was heated to 116° C. for 2.5 hours. The reaction was then stirred at room temperature for 2 days. The solution was concentrated and the residue was taken up in methanol, filtered through diatomaceous earth and concentrated. Purify by silica gel chromatography (2-5% CH2Cl2/methanol) to afford 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (515 mg, 9%).

Workup

  1. concentrationThe solution was concentrated
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated
  4. customPurify by silica gel chromatography (2-5% CH2Cl2/methanol)

Sources & evidence

ORD record
ord-b8ddc1059aa0434ebb052a433807234e
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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