Triethylamine → 3-Bromo-5-phenylethynylpyridine

HRID 606833Notes

Reaction equation

HRID 606833 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1.C(N(CC)CC)C>C(OCC)(=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 693693,5-Dibromopyridine

Product 1

HCID 670476693-Bromo-5-phenylethynylpyridineYield 32%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add phenylacetylene (1.11 mL, 10.10 mmol) dropwise to a mixture of 3,5-dibromopyridine (2.05 g, 8.65 mmol), bis(triphenylphosphine)palladium (II) dichloride (300 mg, 0.427 mmol), and copper (I) iodide (160 mg, 0.840 mmol) in triethylamine (8.50 mL, 60.98 mmol) and stir for 3 h at room temperature. Dilute the reaction mixture with ethyl acetate and wash with a saturated aqueous solution of sodium chloride. Dry (sodium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient of 100:0 to 90:10 hexanes:ethyl acetate, to give the title compound (710 mg, 32%).

Workup

  1. washwash with a saturated aqueous solution of sodium chloride
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with a gradient of 100:0 to 90:10 hexanes

Sources & evidence

ORD record
ord-e0846f5d21cf42dc9419470d6bb02144
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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