Water → 3-(5-Chloro-6-methoxypyridin-2-yl)prop-2-yn-1-ol

HRID 70524Notes

Reaction equation

HRID 70524 reaction equation
C(N(CC)CC)C.Br[C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([Cl:17])=[CH:11][CH:10]=1.[CH2:18]([OH:21])[C:19]#[CH:20].O>[Cu](I)I.C(OCC)(=O)C>[Cl:17][C:12]1[CH:11]=[CH:10][C:9]([C:20]#[C:19][CH2:18][OH:21])=[N:14][C:13]=1[O:15][CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 584523026-Bromo-3-chloro-2-methoxypyridine

Product 1

HCID 584526673-(5-Chloro-6-methoxypyridin-2-yl)prop-2-yn-1-olYield 80%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (70 mL) and bistriphenylphosphinepalladium(II) dichloride (756 mg) were added to 6-bromo-3-chloro-2-methoxypyridine (12.1 g), 2-propyn-1-ol (4.0 g) and copper iodide (210 mg) in a nitrogen atmosphere, and the mixture was stirred at room temperature for four hours. Water and ethyl acetate were added to the reaction solution, followed by filtration. The aqueous layer was adjusted to pH 3 or less with 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3→5:5) to give the title compound as a light brown powder (8.60 g, 80%).

Workup

  1. filtrationfollowed by filtration
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3→5:5)

Sources & evidence

ORD record
ord-747c719673c14319976281b8344aa4fe
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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