2-Bromo-6-(fluoromethyl)pyridine → 2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 334636Notes

Reaction equation

HRID 334636 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6]1)[CH2:2][C:3]#[CH:4].Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][F:23])[N:17]=1>>[F:23][CH2:22][C:18]1[N:17]=[C:16]([C:4]#[C:3][CH2:2][CH2:1][N:5]2[C:13](=[O:14])[N:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]3=[N:6]2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 636564482-(but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 665980172-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 18.1%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-(but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (70 mg, 0.37 mmol, Example 39(A)) and 2-bromo-6-(fluoromethyl)pyridine (78 mg, 0.41 mmol, Example 190(E)). The crude residue was purified by flash chromatography (DCM/MeOH 98:2) to yield 20 mg (67 μmol, 18%) of 2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one as an orange solid (M.P.=106-107° C.).

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-2143e2461212461e8273224028085c24
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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