Sodium hydride → 5-Bromo-2-(cyclopropylmethoxy)pyridine

HRID 330767Notes

Reaction equation

HRID 330767 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Br:8][C:9]1[CH:10]=[CH:11][C:12](F)=[N:13][CH:14]=1>C1COCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 219142795-Bromo-2-(cyclopropylmethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.49 g (6.82 mmol) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmol) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmol) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H2O/FA).

Workup

  1. stirringthe mixture is stirred at r.t. over night
  2. customThe reaction is quenched by the addition of water
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by HPLC (MeOH/H2O/FA)

Sources & evidence

ORD record
ord-a6c1865469b74fa182b2af8aaff5906c
Source dataset
uspto-grants-2014_11
Patent number
US08877741B2

Reaction notes

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