Potassium Carbonate → Methyl 2-((5-bromopyridin-3-yl)methylthio)acetate

HRID 2036841Notes

Reaction equation

HRID 2036841 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8]Cl)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[SH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][S:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 67055984Methyl 2-((5-bromopyridin-3-yl)methylthio)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-5-(chloromethyl)pyridine (from example 199, (1.2 g, 5.8 mmol) in acetonitrile (15 mL) was added K2CO3 (0.97 g, 7.0 mmol) followed by methyl 2-mercaptoacetate (0.57 mL, 6.4 mmol). The resulting solution was stirred at room temperature for 16 h. After this time, the reaction mixture was filtered and the filtrate was diluted with ethyl acetate and washed with water. The organic portion was dried, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (30% ethyl acetate in hexane) to yield methyl 2-((5-bromopyridin-3-yl)methylthio)acetate (1.2 g, 80% yield). LCMS Method Y: retention time 1.66 min; [M+1]=276.0.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water
  4. customThe organic portion was dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8202c32b9ccd4729b0a6fd54f291248e
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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