Sodium hydride → HCID 59526096, compound

HRID 385875Notes

Reaction equation

HRID 385875 reaction equation
[H-].[Na+].[S:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Br)[N:12]=1>O1CCCC1.C(OCC)(=O)C>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:9][CH:6]2[CH2:7][CH2:8][S:3][CH2:4][CH2:5]2)[N:12]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 576296Tetrahydro-2H-thiopyran-4-olHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 59526096HCID 59526096, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.24 g, 5.98 mmol) was suspended in tetrahydrofuran (19.9 mL) and cooled to 0° C. Tetrahydro-2H-thiopyran-4-ol (0.24 g, 1.99 mmol) was added and the reaction was stirred for 30 minutes. 2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (0.5 g, 1.99 mmol) was added and the reaction was warmed to and maintained at ambient temperature overnight. The reaction was diluted with ethyl acetate, quenched slowly with water, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. temperaturethe reaction was warmed to and
  2. temperaturemaintained at ambient temperature overnight
  3. customquenched slowly with water
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e0e1f6c7c7b4455b0cf352d9dac9624
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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