Phenylacetylene → HCID 22050204, compound

HRID 1831893Notes

Reaction equation

HRID 1831893 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:20])[C:8]=1[Br:21])(=O)=O.[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:13]([N:10]1[CH:11]=[CH:12][C:7]([C:31]#[C:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:8]([Br:21])[C:9]1=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 21035297HCID 21035297, compound

Product 1

HCID 22050204HCID 22050204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyl-3-bromo-2-oxo-1,2-dihydropyridin-4-yl trifluoromethanesulfonate (1.0 g) in DMF (5.0 mL) was added phenylacetylene (0.4 mL) and degassed using house vacuum. The reaction flask was then purged with argon, added diisopropylethylamine (0.53 mL), and PdCl2(PPh3)2 (0.35 g) were added. The resulting mixture was stirred at room temperature for 15 min and heated at 65° C. under an argon atmosphere for 3 h. The dark colored reaction mixture was concentrated in vacuo, and the residue was partitioned between EtOAc (50 mL) and 5% aqueous citric acid (25 mL). The organic extracts were washed with water, dried (Na2SO4), filtered, and concentrated to dryness. The resulting material was purified by silica gel flash chromatography using 25% EtOAc in hexanes as the eluent. The appropriate fractions were combined, concentrated under reduced pressure. 1H NMR (CDCl3) δ: 7.57 (m, 2H), 7.38 (m, 8H), 7.21 (d, 1H, J=6.8 Hz), 6.25 (d, 1H, J=6.8 Hz), and 5.16 (d, 2H), ES-MS: m/z=364 (MH+);

Workup

  1. customdegassed
  2. customThe reaction flask was then purged with argon
  3. additionadded diisopropylethylamine (0.53 mL), and PdCl2(PPh3)2 (0.35 g)
  4. additionwere added
  5. temperatureheated at 65° C. under an argon atmosphere for 3 h
  6. concentrationThe dark colored reaction mixture was concentrated in vacuo
  7. customthe residue was partitioned between EtOAc (50 mL) and 5% aqueous citric acid (25 mL)
  8. washThe organic extracts were washed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated to dryness
  12. customThe resulting material was purified by silica gel flash chromatography
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6fb814d681441d597801a4dda69bbf3
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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