Sodium hydride → 5-Bromo-2-(cyclopropylthio)pyridine

HRID 533929Notes

Reaction equation

HRID 533929 reaction equation
[H-].[Na+].[CH:3]1([SH:6])[CH2:5][CH2:4]1.[Br:7][C:8]1[CH:9]=[CH:10][C:11](F)=[N:12][CH:13]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([S:6][CH:3]2[CH2:5][CH2:4]2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27831685-Bromo-2-fluoropyridineHCID 4713099Cyclopropanethiol

Product 1

HCID 576309375-Bromo-2-(cyclopropylthio)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (60% in mineral oil, 2.40 g) in THF (100 mL) was added dropwise cyclopropanethiol (0.25 M in Et2O, 160 mL) at 0° C. After stirring for 30 min, 5-bromo-2-fluoropyridine (3.52 g) was added in portions at 0° C. and then warmed to r.t. slowly. The reaction mixture was stirred at r.t. overnight. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine (50 mL) and dried over Na2SO4. After filtration and evaporation of the solvent, the crude product was obtained and used in next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at r.t. overnight
  2. customThe reaction mixture was quenched with water (30 mL)
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-d37b9c32ba424f93a83b57ad25cdabb5
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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