Cesium carbonate → 2-Bromo-4-(cyclopropylmethoxy)pyridine

HRID 1898599Notes

Reaction equation

HRID 1898599 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.Br[CH2:10][CH:11]1[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:10][CH:11]2[CH2:13][CH2:12]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 178516474HCID 178516474, compound

Product 1

HCID 575166372-Bromo-4-(cyclopropylmethoxy)pyridineYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromopyridin-4-ol (1.6 g, 9.2 mmol) and (bromomethyl)cyclopropane (1.61 g, 12.0 mmol) in DMF (12 mL) in a microwave vial was added cesium carbonate (4.19 g, 12.9 mmol). The vial was sealed and heated in a microwave reactor at 120° C. for 4 h. The reaction mixture was cooled to room temperature, quenched with water and extracted with EtOAc (2×). The combined organics were washed with sat'd NaCl then dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (20-50% EtOAc/heptane) to give 1.45 g (69%) of 2-bromo-4-cyclopropylmethoxy-pyridine as a yellow oil.

Workup

  1. customThe vial was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organics were washed with sat'd NaCl
  6. dry with materialthen dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 chromatography (20-50% EtOAc/heptane)

Sources & evidence

ORD record
ord-e724b800293e465890de883ed1ba0029
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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