Sodium hydride → HCID 104809848, compound

HRID 712655Notes

Reaction equation

HRID 712655 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH2:17]Br)[CH:16]=1.[NH4+].[Cl-]>CN(C=O)C>[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH2:17][O:9][CH:6]2[CH2:7][CH2:8][O:3][CH2:4][CH2:5]2)[CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74956Tetrahydro-4H-pyran-4-olHCID 149329483-Bromo-5-(bromomethyl)pyridine

Product 1

HCID 104809848HCID 104809848, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 60% NaH (640 mg, 16 mmol) in DMF (80 mL) is added tetrahydro-pyran-4-ol (1.6 g, 16 mmol) at 0° C. After the mixture is stirred at room temperature for 0.5 h, 3-bromo-5-bromomethyl-pyridine (1.6 g, 6.4 mmol) is added at 0° C. under N2 atmosphere. The mixture is stirred at room temperature for 16 hrs. Then saturated NH4Cl aqueous solution is used to quench the reaction and the mixture is extracted with DCM. The organic layers are combined, dried over Na2SO4, filtered and concentrated. The crude product is purified by flash column chromatography to give 700 mg of 3-bromo-5-(tetrahydro-pyran-4-yloxymethyl)-pyridine.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hrs
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture is extracted with DCM
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-721c51aa3b7a4e568ea9d5bcb15c2a80
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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