Triethylamine → HCID 18372930, compound

HRID 865419Notes

Reaction equation

HRID 865419 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:10]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[CH:22])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.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]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[C:22][C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 561991HCID 561991, compoundHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 18372930HCID 18372930, compoundYield 68.4%

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 (30.0 g), 7-phenyl-1-heptyne (26.8 g), triethylamine (48.9 g), bis(triphenylphosphine)palladium(II)chloride (2.3 g, 2%), and copper(I)iodide (0.31 g, 1%) in dry tetrahydrofuran (100 ml) was heated under nitrogen at 55° C. for 70 hrs. The reaction mixture was cooled to ambient temperature, filtered, and the filtrate was washed with ethyl acetate. The filtrate was evaporated. The residue was dissolved in ethyl acetate, the solution washed with half-saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the filtrate was concentrated. The residue was flash chromatographed on silica gel, eluting with 0.5% to 2%-ethyl acetate:hexane. The appropriate fractions were collected and concentrated to yield 29.5 g of the product.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with ethyl acetate
  3. customThe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution washed with half-saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationthe filtrate was concentrated
  8. customchromatographed on silica gel
  9. washeluting with 0.5% to 2%-ethyl acetate
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b47ebd43c26d43c69062129ee6b382e1
Source dataset
uspto-grants-1996_10
Patent number
US05565584

Reaction notes

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