Dimethylformamide → 2-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 731731Notes

Reaction equation

HRID 731731 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]([C:9]1[CH:17]=[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1)([CH3:8])[CH3:7].[OH-].[Na+].CN([CH:23]=[O:24])C>>[CH:6]([C:9]1[C:17]([CH:23]=[O:24])=[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 143032672-Isopropylpyrazolo[1,5-a]pyridine-3-carbaldehydeYield 82%

Procedure

Upon stirring 3 mL of DMF at room temperature, neat phosphorous oxychloride (0.8 mL 1.3 equivalents) was added dropwise. The resulting mixture was stirred at room temperature for 10 minutes, followed by dropwise addition of neat 2-isopropylpyrazolo[1,5-a]pyridine (1 g, 1 equivalent). The solution was stirred at room temperature for 19 hours and poured into 100 mL of ice water. The pH of the aqueous solution was adjusted to 8 using solid NaOH. The precipitate formed was collected by filtration and dried under reduced pressure to furnish 2-isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde (0.97 g, 82% yield) as a white solid. Compound 1073.

Workup

  1. stirringThe solution was stirred at room temperature for 19 hours
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b018040e0f2049859264b5e3efc50b53
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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