Sodium hydride → 4-Bromo-2-[(oxan-4-yl)oxy]pyridine

HRID 1894181Notes

Reaction equation

HRID 1894181 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[Br:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13](Cl)[CH:12]=1>C1COCC1>[Br:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([O:3][CH:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 38477704-Bromo-2-chloropyridine

Product 1

HCID 592777554-Bromo-2-[(oxan-4-yl)oxy]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (0.4 g, 10 mmol) in THF (20 ml) at 0° C. was added 4-hydroxytetrahydropyran (1.02 ml, 10 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 30 mins before 4-bromo-2-chloropyridine (0.89 ml, 8.0 mmol) was added dropwise. The reaction mixture was stirred for 18 h before being quenched with EtOH (1 ml), partitioned between CH2Cl2 and H2O and extracted CH2Cl2 (×2). The organics were combined, dried (MgSO4), filtered and the solvent removed in vacuo. Purified by column chromatography to afford 4-Bromo-2-(tetrahydro-pyran-4-yloxy)-pyridine MS: [MH]+ 258, 260

Workup

  1. additionwas added dropwise
  2. custombefore being quenched with EtOH (1 ml)
  3. custompartitioned between CH2Cl2 and H2O
  4. extractionextracted CH2Cl2 (×2)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customPurified by column chromatography

Sources & evidence

ORD record
ord-0ce7bfbe8fb4445982de9b0a178ae894
Source dataset
uspto-grants-2013_08
Patent number
US08513276B2

Reaction notes

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