Triethylamine → Tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate

HRID 1006035Notes

Reaction equation

HRID 1006035 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=1)#[CH:17].C(N(CC)CC)C>CN(C=O)C.[Cu](I)(I)I>[C:10]1([CH:9]=[CH:8][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[C:17]#[C:16][C:18]2[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13965008Tert-butyl 4-ethynylbenzoateHCID 539315873-Bromo-4-(2-phenylethenyl)pyridine

Product 1

HCID 54016878Tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoateYield 33%

Reagents, catalysts & solvents 2

HCID 178506583HCID 178506583, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

3-Bromo-4-(2-phenylethenyl)pyridine (0.74 g, 2.9 mmol) was dissolved in DMF (1.4 ml). The solution was treated with tert-butyl 4-ethynylbenzoate (0.93 g, 4.6 mmol), copper (III) iodide (0.023 g, 0.21 mmol) and triethylamine (0.64 g, 6.3 mmol). The reaction mixture was degassed by bubbling through argon and the catalyst, bistriphenyl phosphinepalladium dichloride (0.03 g, 0.043 mmol), was added. The reaction was heated to 90-100° C. for 3 hours and then partitioned between ethyl acetate and water. The organic layer was washed with water (3×), dried (MgSO4) and evaporated. The residue was purified by chromatography (eluting with ethylacetate/hexane) to give tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate as a dark oil (0.36 g, 33%).

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling through argon
  3. additionthe catalyst, bistriphenyl phosphinepalladium dichloride (0.03 g, 0.043 mmol), was added
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with water (3×)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by chromatography (eluting with ethylacetate/hexane)

Sources & evidence

ORD record
ord-7243a44edaff415ab5ed24af00dea905
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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