2-Bromopyridine → 2-(4-(pyridin-2-yl)but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 422285Notes

Reaction equation

HRID 422285 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]=[CH:18][N:17]=1>>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:4]#[C:3][CH2:2][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

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 636564482-(but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 665981432-(4-(pyridin-2-yl)but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 23.5%

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) and 2-bromopyridine (65 mg, 0.41 mmol). The crude residue was purified by flash chromatography (DCM/MeOH 98:2) to yield 23 mg (87 μmol, 23%) of 2-(4-(pyridin-2-yl)but-3-ynyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one as a yellow solid (M.P.=95.5-96° C.).

Workup

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

Sources & evidence

ORD record
ord-01860ca09c5849dfa56cd991f928cb80
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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