1-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol → 1-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one

HRID 1269068Notes

Reaction equation

HRID 1269068 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[O:16][CH:17]=[CH:18][C:19]=3[CH3:20])[C:10]([CH:11]([OH:14])[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[O:16][CH:17]=[CH:18][C:19]=3[CH3:20])[C:10]([C:11](=[O:14])[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 184465961-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol

Product 1

HCID 184465971-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (12.29 g, 42.9 mmol) was dissolved in dichloromethane (200 mL) and manganese dioxide (112 g, 1.29 mol) was added. This slurry was stirred at room temperature for 2 hours. The manganese dioxide was removed by filtration and the filtrate was concentrated to a solid. This solid was purified by flash chromatography (dichloromethane) to give 1-[7-chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (7.53 g, 62%) as a white solid. 1H-NMR (CDCl3): δ 8.37 (d, 1H), 7.48 (m, 2H), 7.19 (d, 1H), 6.41 (d, 1H), 3.12 (s, 1H), 2.20 (s, 3H). MS m/z 285 (M+1).

Workup

  1. customThe manganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated to a solid
  3. customThis solid was purified by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-8c8e231afec242e1977a7ed12513bea1
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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