Isobutylene oxide → 4-Bromo-1-(2-hydroxy-2-methylpropyl)-2(1H)-pyridinone

HRID 1408973Notes

Reaction equation

HRID 1408973 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH3:9][C:10]1([CH3:13])[CH2:12][O:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:9][C:10]([OH:11])([CH3:13])[CH3:12])[C:4](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 8171154-Bromo-2-hydroxypyridine

Product 1

HCID 596357304-Bromo-1-(2-hydroxy-2-methylpropyl)-2(1H)-pyridinoneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 4-bromopyridin-2(1H)-one (200 mg, 1.15 mmol), 2,2-dimethyloxirane (208 μL, 2.34 mmol) in DMF (2 mL) was added K2CO3 (320 mg, 2.32 mmol) and heated at 120° C. for 30 min in a microwave reactor. The reaction mixture was partitioned between ethyl acetate and water and the layers were separated. The organic extract was dried (Na2SO4), filtered and concentrated to afford a crystalline solid (240 mg, 85% yield) which was used without further purification. 1H NMR (400 MHz, CCl3D) δ 7.25 (d, J=7.5 Hz, 1H), 6.88 (d, J=2.0 Hz, 1H), 6.38 (dd, J=7.3, 2.2 Hz, 1H), 4.01 (s, 2H), 3.43 (br s, 1H), 1.28 (m, 6H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ece01e9176741fc90339746343f627d
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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