4-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin → 2-Trifluoromethyl-4-formyl-7-iodo-pyrazolo[1,5-a]pyridine

HRID 2357901Notes

Reaction equation

HRID 2357901 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[C:6]2[C:7]([CH2:12][OH:13])=[CH:8][CH:9]=[C:10]([I:11])[N:5]2[N:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:14]=[C:6]2[C:7]([CH:12]=[O:13])=[CH:8][CH:9]=[C:10]([I:11])[N:5]2[N:4]=1

Participants

4

Reactant 1

HCID 593893564-Hydroxymethyl-7-iodo-2-trifluoromethylpyrazolo[1,5-a]pyridin

Product 1

HCID 593892992-Trifluoromethyl-4-formyl-7-iodo-pyrazolo[1,5-a]pyridineYield 91.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound of Example 112 (3.26 g) was dissolved in dichloromethane (50.0 mL). To this solution, activated manganese dioxide (8.29 g) was added and the mixture was stirred at room temperature for 14 hours. Subsequently, the reaction mixture was filtered through Celite and the filtrate was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1) afforded the title compound as a yellow powder (2.97 g).

Workup

  1. additionwas added
  2. filtrationSubsequently, the reaction mixture was filtered through Celite
  3. customthe filtrate was evaporated
  4. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c6d8234b0c7f48da8c6cc899aff1e09b
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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