Triethylamine → 6-(1-Undecynyl)pyridine-2-carboxaldehyde

HRID 1734798Notes

Reaction equation

HRID 1734798 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:10]([C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1)#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 752491-UndecyneHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 153806466-(1-Undecynyl)pyridine-2-carboxaldehydeYield 84.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-bromopyridine-2-caboxaldehyde (15.0 g), 1-undecyne (12.9 g), triethylamine (24.5 g), bis(triphenylphosphine)palladium(II)chloride (1.1 g, 2% ), and copper(I)iodide (0.15g, 1%) in dry tetrahydrofuran (60 ml) was heated under nitorgen at 55° C. for 10 hrs. The reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, and the solution was washed with half-saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed on silica gel, eluting with 0%-2%-ethyl acetate:hexane. The appropriate fractions were collected and evaporated to yield 17.5 g (84.0%) of product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with ethyl acetate
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with half-saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customchromatographed on silica gel
  10. washeluting with 0%-2%-ethyl acetate
  11. customThe appropriate fractions were collected
  12. customevaporated

Sources & evidence

ORD record
ord-57ebd2a437524633b182d9a14e495a06
Source dataset
uspto-grants-1996_07
Patent number
US05534636

Reaction notes

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