Potassium Carbonate → HCID 57531256, compound

HRID 1454995Notes

Reaction equation

HRID 1454995 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][CH:11]1[CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:7]([O:8][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinolHCID 81503Bromomethylcyclopropane

Product 1

HCID 57531256HCID 57531256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-bromo-pyridin-3-ol Compound 1a (6.4 g, 36.8 mmol) was dissolved into DMF (100 mL), then bromomethyl-cyclopropane Compound 1b (5.0 g, 37 mmol) and K2CO3 (7.5 g, 54.3 mmol) were added. The mixture was stirred and heated at 80° C. for 2 hrs. Excess DMF was removed on a rotary evaporator. The brown residue was mixed with Et2O (150 mL), then washed with H2O and dried over Na2SO4. The solvent was evaporated from the dry solution to provide 2-bromo-3-cyclopropylmethoxy-pyridine Compound 1c (7.04 g, yield 84%).

Workup

  1. customExcess DMF was removed on a rotary evaporator
  2. additionThe brown residue was mixed with Et2O (150 mL)
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated from the dry solution

Sources & evidence

ORD record
ord-af982aa15618476984b5df80ab4bd3c5
Source dataset
uspto-grants-2009_01
Patent number
US07482348B2

Reaction notes

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