5-Bromo-2-hydroxypyridine → HCID 66675399, compound

HRID 422526Notes

Reaction equation

HRID 422526 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10]O.[Br:12][C:13]1[CH:14]=[CH:15][C:16](=[O:19])[NH:17][CH:18]=1>>[Br:12][C:13]1[CH:14]=[CH:15][C:16](=[O:19])[N:17]([CH2:10][CH2:9][C:8]#[C:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:18]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](=[O:19])[N:17]([C:10]#[C:9][CH2:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 5995285-Bromo-2-hydroxypyridineHCID 110080634-(Pyridin-2-yl)but-3-yn-1-ol

Product 2

HCID 66598429HCID 66598429, compoundHCID 66675399HCID 66675399, compoundYield 46.2%

Procedure

The title compound was prepared in accordance with the general method of Example 109(D), from 4-(pyridin-2-yl)but-3-yn-1-ol (700 mg, 4.76 mmol, Example 3(A)) and 5-bromo-1H-pyridin-2-one (870 mg, 5.00 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 334 mg (1.10 mmol, 23%) of 5-bromo-1-(4-pyridin-2-yl-but-ynyl)-1H-pyridin-2-one.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record
ord-9bef3d7972fa46d6ab2443468c38f90b
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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