Isobutanol → 2-Bromo-6-(2-methylpropoxy)pyridine

HRID 2104994Notes

Reaction equation

HRID 2104994 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[Na].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[N:9]=1>CCOC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:4][CH2:3][CH:2]([CH3:5])[CH3:1])[N:9]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 122742,6-DibromopyridineHCID 5360545Sodium2×

Product 1

HCID 639640402-Bromo-6-(2-methylpropoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-methylpropan-1-ol (1 mL), was added sodium (36 mg, 1.56 mmol). The mixture was stirred at 70° C. until sodium was ˜75% consumed, then 1 mL THF and the mixture was stirred an additional 15 min. To this mixture, 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 185 mg of Intermediate 162.1 as a colorless oil. LCMS (2 min gradient) RT=1.98 min, 230.2 (M+H)+.

Workup

  1. customconsumed
  2. stirringThe mixture was stirred at 90° C. for 2 h
  3. washThe organic phase was washed with water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-286834f81fec4c809aa516347d784877
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…