1-Propanol → 2-Bromo-6-propoxypyridine

HRID 2104993Notes

Reaction equation

HRID 2104993 reaction equation
[CH2:1]([O-:4])[CH2:2][CH3:3].[Na+].[Na].C(O)CC.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[N:13]=1>CCOC(C)=O>[Br:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:4][CH2:1][CH2:2][CH3:3])[N:13]=1

Participants

6

Reactant 4

HCID 10311-PropanolHCID 122742,6-DibromopyridineHCID 5360545SodiumHCID 236693631-Propanol, sodium salt (1:1)

Product 1

HCID 235573982-Bromo-6-propoxypyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a sodium propan-1-olate solution, prepared by addition of sodium (36 mg, 1.58 mmol) to propanol (1 mL), was added 2,6-dibromopyridine (250 mg, 1.06 mmol). The mixture was stirred at 90° C. for 2 h, then was diluted with EtOAc. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 189 mg of Intermediate 161.1 as a colorless oil. LCMS (2 min gradient) RT=1.82 min, 216.1 (M+H)+.

Workup

  1. washThe organic phase was washed with water (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-3efdbc6ac007497d93908a3c5ae8fbbf
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…