Water → 5-Bromo-2-(tetrahydro-2H-pyran-4-yloxy)pyridine

HRID 57547

Reaction equation

HRID 57547 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[CH:13][C:14](Cl)=[N:15][CH:16]=1.O>CN(C=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 219143915-Bromo-2-(tetrahydro-2H-pyran-4-yloxy)pyridineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

tetrahydro-2H-pyran-4-ol (850 mg, 8.32 mmol) was dissolved in DMF (10 mL), cooled to 0° C., NaH (500 mg, 10.4 mmol) was added and stirred for 45 minutes at room temperature, then 5-bromo-2-chloropyridine (2 g, 10.4 mmol) was added and the mixture was stirred overnight at 60° C. The mixture was poured into water, extracted by EA, the organic layer was washed by brine, dried over Na2SO4, concentrated and purified by flash chromatography, gave 1.7 g white solid. MS: (m/z): 258 (M−H)+, 260 (M+H)+

Workup

  1. stirringthe mixture was stirred overnight at 60° C
  2. extractionextracted by EA
  3. washthe organic layer was washed by brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7694a110ba134784a421258096b9983e
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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