2,6-Dibromopyridine → HCID 18673791, compound

HRID 1636184Notes

Reaction equation

HRID 1636184 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH2:9][OH:10])([CH3:6])([CH3:5])[CH3:4].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[N:13]=1>C1(C)C=CC=CC=1.O>[C:3]([O:7][CH2:8][CH2:9][O:10][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([Br:11])[N:13]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 122742,6-DibromopyridineHCID 242322-(Tert-butoxy)ethan-1-olHCID 24758Sodium hydride

Product 1

HCID 18673791HCID 18673791, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium hydride (6.8 g, 60% dispersion in mineral oil, 0.169 mol) was added portionwise to an ice-cold solution of 2-(tert-butoxy)ethanol (20.0 g, 0.169 mol) in toluene (500 ml) under nitrogen, and the solution stirred for 30 minutes whilst warming to ambient temperature. 2,6-Dibromopyridine (40.0, 0.169 mol) was added, and the reaction heated under reflux for 3 hours. The mixture was allowed to cool to ambient temperature and was diluted with water (100 ml), and extracted with ethyl acetate (2×400 ml). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow oil (quantitative). 1H nmr (CDCl3, 400 MHz) δ: 1.21 (s, 9H), 3.67 (t, 2H), 4.40 (t, 2H), 6.68 (d, 1H), 7.05 (d, 1H), 7.38 (t, 1H). LRMS: m/z 296/298 (M+23)+.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool to ambient temperature
  4. extractionextracted with ethyl acetate (2×400 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-818b15df9b57483ca65c61638d928433
Source dataset
uspto-grants-2003_01
Patent number
US06511993B1

Reaction notes

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