HCID 18446594, compound → HCID 18446595, compound

HRID 1269073Notes

Reaction equation

HRID 1269073 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[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][CH:19]=3)[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 18446594HCID 18446594, compound

Product 1

HCID 18446595HCID 18446595, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1-[7-Chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (3.63 g, 13.3 mmol) was dissolved in dichloromethane (200 mL) and manganese dioxide (34.7 g, 399 mmol) 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, 1-[7-chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (1.99 g, 55%). 1H NMR (CDCl3): δ 8.54 (d, 1H), 7.65 (d, 1H), 7.62 (d, 1H), 7.49 (t, 1H), 7.21 (d, 1H), 6.58 (m, 1H), 3.35 (s, 1H). MS m/z 271 (M+1).

Workup

  1. customThe manganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated to a solid, 1-[7-chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (1.99 g, 55%)

Sources & evidence

ORD record
ord-101250599ad44cb396a257bba9d00b43
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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