Phenylacetylene → HCID 22050204, compound

HRID 1866877Notes

Reaction equation

HRID 1866877 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+); HR-MS m/z (MH+) calcd C20H15NOBr 364.0337, found 364.0337.

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-292f45d122d14583818ddd79628e2c82
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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