2-Bromo-3-pyridinol → HCID 57531256, compound

HRID 1517590Notes

Reaction equation

HRID 1517590 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:12][CH:13]1[CH2:15][CH2:14]1>CN(C)C=O>[Br:1][C:2]1[C:7]([O:8][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydrideHCID 81503Bromomethylcyclopropane

Product 1

HCID 57531256HCID 57531256, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-3-pyridinol (500 mg, 2.83 mmol;) in dimethylformamide (3 mL) is added at 0° C. 60% sodium hydride in mineral oil (169.81 mg, 4.25 mmol). The mixture is stirred at that temperature for 15 min and bromomethylcyclopropane (329.66 μL, 3.40 mmol) is added. Then the reaction is stirred at room temperature for 1 h and quenched with water and extracted with ethyl acetate. The organic layer is separated, washed with brine, dried over magnesium sulfate and the solvent evaporated in vacuo. The crude is passed through a short silica gel plug and the compound was eluted with dichloromethane to yield 23% of the title compound. MS (m/z): 228 (M+1), 230 (M+3).

Workup

  1. stirringThen the reaction is stirred at room temperature for 1 h
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent evaporated in vacuo
  8. washthe compound was eluted with dichloromethane

Sources & evidence

ORD record
ord-d39a07fd96a04eb2b9aae522c5eded6c
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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