Cyclohexanol → 5-Bromo-2-(cyclohexyloxy)pyridine

HRID 1747950Notes

Reaction equation

HRID 1747950 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[CH:13][C:14](Cl)=[N:15][CH:16]=1>CN(C)C(=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 613756815-Bromo-2-(cyclohexyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

Cyclohexanol (3.99 mL) was added to a mixture of NaH (60%, 1.50 g) in N,N-dimethylacetoamide (10 mL) at 0° C. The mixture was stirred at room temperature for 30 min. The solution of 5-bromo-2-chloropyridine (6.00 g) in N,N-dimethylacetoamide (10 mL) was added and the mixture was stirred at 100° C. for 1.5 hr. The mixture was quenched with water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (7.67 g) as colorless oil.

Workup

  1. stirringthe mixture was stirred at 100° C. for 1.5 hr
  2. customThe mixture was quenched with water at room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-2c0afc1e58c14f6488138789e2d5db94
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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