Water → 1-(6-Bromo-2-methoxypyridin-3-yl)ethan-1-one

HRID 70551Notes

Reaction equation

HRID 70551 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[C:18](=[O:20])[CH3:19].O>C(OCC)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:18](=[O:20])[CH3:19])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 582361006-bromo-3-iodo-2-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 584525111-(6-Bromo-2-methoxypyridin-3-yl)ethan-1-oneYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 6-bromo-3-iodo-2-methoxypyridine (500 mg) in diethyl ether (15 mL) was cooled to −80° C. in a nitrogen atmosphere, and n-butyllithium (2.6 M, 0.735 mL) were added dropwise. After stirring at the same temperature for one hour, N,N-dimethylacetamide (0.37 mL) was added dropwise. The mixture was warmed to −40° C. over 1.5 hours to complete the reaction. Water and ethyl acetate was added to the reaction system. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give the title compound as a colorless powder (284 mg, 78%).

Workup

  1. additionwere added dropwise
  2. customthe reaction
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-4b2c1a87231a4546b95aeb3418fbb55a
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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