Dimethylformamide → 2-Bromo-5-(cyclopropylmethoxy)pyridine

HRID 1026339Notes

Reaction equation

HRID 1026339 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH:11]1[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 578217962-Bromo-5-(cyclopropylmethoxy)pyridineYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-bromopyridin-3-ol (10.0 g), (bromomethyl)cyclopropane (7.76 g), potassium carbonate (11.9 g), and DMF (100 mL) was stirred at 60° C. overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (12.0 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e73a977f534d479799b49d3982f0798e
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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