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

HRID 2104991Notes

Reaction equation

HRID 2104991 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[Na].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[N:9]=1>C1COCC1.CCOC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)[N:9]=1

Participants

6

Reactant 3

HCID 122742,6-DibromopyridineHCID 76218CyclobutanolHCID 5360545Sodium

Product 1

HCID 457875272-Bromo-6-(cyclobutyloxy)pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To cyclobutanol (1 mL), was added sodium (36 mg, 1.56 mmol). When the sodium was consumed, the mixture was diluted with 1 mL THF and 2,6-dibromopyridine (250 mg, 1.06 mmol). The mixture was stirred at 90° C. for 3 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 106 mg of 158.1 as a colorless oil. LCMS (2 min gradient) RT=1.87 min, 228.17 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3a1cb5be78b04cecb734423aedd9aa93
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…