2,6-Dibromopyridine → 2-Bromo-6-(cyclobutyloxy)pyridine

HRID 1183495Notes

Reaction equation

HRID 1183495 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1>C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)[N:10]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 76218Cyclobutanol

Product 1

HCID 457875272-Bromo-6-(cyclobutyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Cyclobutanol (0.470 mL, 6 mmol) was dissolved in toluene (2 mL) and sodium hydride (60% in mineral oil, 0.240 g, 6 mmol) was added. The reaction was stirred at room temperature for 10 minutes then 2,6-dibromo-pyridine (0.710 g, 3 mmol) was added. The reaction was heated to 110° C. for 16 hours then cooled to room temperature, filtered through Celite, and purified on silica gel (0-5% EtOAc in hexanes) to give the title compound.

Workup

  1. temperatureThe reaction was heated to 110° C. for 16 hours
  2. temperaturethen cooled to room temperature
  3. filtrationfiltered through Celite
  4. custompurified on silica gel (0-5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-891672604faa41d2b1f08dabf71b3a63
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

Loading…