2-Chloro-4-methylpyridine → HCID 86657914, compound

HRID 2359016Notes

Reaction equation

HRID 2359016 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[S:14][C:13]([C:15](OCC)=[O:16])=[CH:12][CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:9][C:10]1[S:14][C:13]([C:15](=[O:16])[CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 772482-Chloro-4-methylpyridineHCID 521808Ethyl 5-chlorothiophene-2-carboxylateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 86657914HCID 86657914, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-chloro-4-methylpyridine (15.6 mmol) and ethyl 5-chlorothiophene-2-carboxylate (17.2 mmol) in anhydrous THF (17 mL) at 0° C., under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1 molar solution in hexanes, 31.3 mmol). The mixture was stirred 2 h at 5° C. The solvent was then evaporated and the residue was dissolved in a mixture of water and dichloromethane. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried with MgSO4, and concentrated under reduced pressure to afford 4.3 g (96% yield) of 1-(5-chloro-2-thienyl)-2-(2-chloropyridin-4-yl)ethanone.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue was dissolved in a mixture of water and dichloromethane
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4adfc909f0154b0ca8435d6ad021c949
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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