Isopropanol → 4-Bromo-2-isopropoxypyridine

HRID 445651Notes

Reaction equation

HRID 445651 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6](Cl)[CH:5]=1.[CH:11]([OH:14])([CH3:13])[CH3:12]>>[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:14][CH:11]([CH3:13])[CH3:12])[CH:5]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 38477704-Bromo-2-chloropyridine

Product 1

HCID 457878974-Bromo-2-isopropoxypyridine

Procedure

To isopropanol (12 ml) under Ar was added 55% sodium hydride in oil (343 mg, 7.86 mmol) in two portions. After 30 min stirring at rt was added 4-bromo-2-chloropyridine (Aldrich, Buchs, Switzerland, 1.01 g, 5.24 mmol) and the reaction mixture was heated with microwave irradiation to 150° C. for 30 min. The reaction mixture was concentrated, quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by MPLC (heptane/EtOAc 0% to 20%) to give the title compound as an oil. (HPLC: tR 3.58 min (Method A); M+H=216, 218 MS-ES)

Workup

  1. temperaturethe reaction mixture was heated with microwave irradiation to 150° C. for 30 min
  2. concentrationThe reaction mixture was concentrated
  3. customquenched with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by MPLC (heptane/EtOAc 0% to 20%)

Sources & evidence

ORD record
ord-ff6b2feb2b0046f5b0a11f89031dec9c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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