Triethylamine → HCID 15380643, compound

HRID 865415Notes

Reaction equation

HRID 865415 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][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].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][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 123961-HexadecyneHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 15380643HCID 15380643, compoundYield 53.5%

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-bromo-2-pyridinecarboxaldehyde (12.3 g), 1-hexadecyne (16.1 g), triethylamine (20.0 g), bis(triphenylphosphine)palladium(II)chloride (0.92 g), and copper(I)iodide (0.13 g) in dry tetrahydrofuran (55 ml) was heated at 50° C. for 29 hrs, under nitrogen. The reaction mixture was cooled to room temperature, filtered, and the filter cake was washed with ethyl acetate. The filtrate was evaporated and the residue was taken up in ethyl acetate (100 ml). The mixture was washed with 1:1 -water:saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was flash chromatographed on silica gel, eluting with 1% ethyl acetate:hexanes. The appropriate fractions were collected and 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 evaporated to give 11.5 g (53.5%) of product, mp 38.5°-40° C.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with ethyl acetate
  3. customThe filtrate was evaporated
  4. washThe mixture was washed with 1:1 -water
  5. dry with materialsaturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customchromatographed on silica gel
  9. washeluting with 1% ethyl acetate
  10. customThe appropriate fractions were collected
  11. customevaporated
  12. dissolutionThe residue was dissolved in ethyl acetate
  13. washthe solution was washed with half-saturated sodium chloride solution
  14. dry with materialdried over anhydrous magnesium sulfate
  15. filtrationfiltered
  16. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2efeff7aadf94a818e541b3181feff07
Source dataset
uspto-grants-1996_10
Patent number
US05565584

Reaction notes

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