2-Methoxyethanol → 5-Bromo-2-(2-methoxyethoxy)pyridine

HRID 76127Notes

Reaction equation

HRID 76127 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1>C1COCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 225027175-Bromo-2-(2-methoxyethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.25 mL 2-methoxyethanol (3.17 mmol) are added to a mixture of 80 mg (3.17 mmol) sodium hydride in 5 mL THF. The reaction mixture is stirred at r.t. for 10 min before 500 mg (2.11 mmol) 2,5-dibromopyridine are added. After 5 h at 75° C. the reaction mixture is diluted with half sat.aq. NaHCO3 solution and extracted with EtOAc. The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc 85/15).

Workup

  1. additionare added
  2. additionAfter 5 h at 75° C. the reaction mixture is diluted with half sat.aq
  3. extractionNaHCO3 solution and extracted with EtOAc
  4. dry with materialThe organic layer is dried with MgSO4
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc 85/15)

Sources & evidence

ORD record
ord-c63a91032d1f4a6fa94b0f90a8a2f920
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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