HCID 18446590, compound → HCID 18446591, compound

HRID 1269078Notes

Reaction equation

HRID 1269078 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[C:16]([CH:17]([OH:20])[C:18]#[CH:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[N:9]3[N:8]=2)=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[O:6][C:5]([C:7]2[C:16]([C:17](=[O:20])[C:18]#[CH:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[N:9]3[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18446590HCID 18446590, compound

Product 1

HCID 18446591HCID 18446591, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described in Example 25 from 2-(5-bromo-2-furyl)-7-chloropyrazolo[1,5-a]pyridine-3-carbaldehyde (2.54 g, 7.8 mmol) was obtained 1-[2-(5-bromo-2-furyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol. To the solution of 1-[2-(5-bromo-2-furyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol in dichloromethane was added manganese dioxide as described in example 25. 1-[2-(5-Bromo-2-furyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (0.86 g, two steps 32%) was obtained as a yellow solid. 1H NMR (CDCl3): δ 8.53 (d, 1H), 7.52–7.48 (m, 2H), 7.22 (d, 1H), 6.51 (d, 1H), 3.36 (s, 1H). MS m/z 349 (M+1).

Sources & evidence

ORD record
ord-db753e9a64d24b8ba95ed9adb2df05cc
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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