Bromocyclopentane → HCID 62721387, compound

HRID 524393Notes

Reaction equation

HRID 524393 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([SH:8])=[N:6][CH:7]=1.Br[CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8728BromocyclopentaneHCID 178527717HCID 178527717, compound

Product 1

HCID 62721387HCID 62721387, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-bromopyridine-2-thiol (0.5 g, 3.44 mmol) was dissolved in anhydrous DMSO (10 mL). CS2CO3 (2.23 g, 6.89 mmol) was added and stirred for 5 minutes followed by addition of bromocyclopentane (0.73 mL, 6.89 mmol). The reaction mixture was stirred for 30 min. at room temperature. The reaction mixture was poured on ice cold water (25 mL) and extracted with MTBE (2×25 mL) washed with water and brine dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product which was purified by column chromatography over silica gel using 2-5% ethyl acetate in hexanes as eluent to provide 5-bromo-2-cyclopentylsulfanyl-pyridine (0.7 g).

Workup

  1. stirringThe reaction mixture was stirred for 30 min. at room temperature
  2. additionThe reaction mixture was poured on ice cold water (25 mL)
  3. extractionextracted with MTBE (2×25 mL)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a crude product which
  9. customwas purified by column chromatography over silica gel using 2-5% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-27eecee8587e4c1a90b430a9fd232db3
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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