Quinoline → HCID 69414064, compound

HRID 1295883Notes

Reaction equation

HRID 1295883 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[C:5]([O:20][C:21]#[C:22][CH:23]([CH3:25])[CH3:24])[CH:4]=1.N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C1C=CC=CC=1.[Pd].C([O-])([O-])=O.[Ca+2]>[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[C:5]([O:20][CH:21]=[CH:22][CH:23]([CH3:25])[CH3:24])[CH:4]=1

Participants

6

Reactant 2

HCID 7047QuinolineHCID 69415058HCID 69415058, compound

Product 1

HCID 69414064HCID 69414064, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 12000666Calcium Palladium CarbonateCatalystHCID 131709914Lindlars catalystCatalystHCID 241BenzeneSolvent

Procedure

5% Pd/CaCO3 poisoned with lead (Lindlar's catalyst) (1.37 g, 0.642 mmol) was added to a solution of (104) (2.17 g, 6.42 mmol) and quinoline (3.5 mL) in benzene (200 mL). The reaction flask was evacuated, and then backfilled with H2 from a balloon. The reaction was stirred under H2 for 2 h. (The reaction can be monitored by the 1HNMR of small aliquots which have been filtered through celite and concentrated, observing the disappearance of the alkyne proton or the appearance of the olefin protons.) After 2 h, more Pd catalyst was added (0.5 g) and the reaction was stirred 1.5 h more under H2. The reaction was filtered through a pad of celite, washed with EtOAc (300 mL) and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL), washed with 2M HCl (4×200 mL) and sat. NaHCO3, dried (Na2SO4), and concentrated under reduced pressure to yield 1.65 g (76%) of a yellow solid. (LH-63-17)

Workup

  1. customThe reaction flask was evacuated
  2. customThe reaction
  3. filtrationhave been filtered through celite and
  4. concentrationconcentrated
  5. wait) After 2 h
  6. additionmore Pd catalyst was added (0.5 g)
  7. stirringthe reaction was stirred 1.5 h more under H2
  8. filtrationThe reaction was filtered through a pad of celite
  9. washwashed with EtOAc (300 mL)
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  12. washwashed with 2M HCl (4×200 mL) and sat. NaHCO3
  13. dry with materialdried (Na2SO4)
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c27838d5df7e4959b2f580d93cec9de1
Source dataset
uspto-grants-2007_07
Patent number
US07244760B2

Reaction notes

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