Diisopropylethylamine → HCID 58608093, compound

HRID 2243589Notes

Reaction equation

HRID 2243589 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([O:14]CC2C=CC=CC=2)=[C:10](I)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:33]1([C:39]#[C:40][Si:41]([CH2:46][CH3:47])([CH2:44][CH3:45])[CH2:42][CH3:43])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10]2[C:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:40]([Si:41]([CH2:46][CH3:47])([CH2:42][CH3:43])[CH2:44][CH3:45])[O:23][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 11085224HCID 11085224, compoundHCID 22050830HCID 22050830, compound

Product 1

HCID 58608093HCID 58608093, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
108 °C

Procedure

To a solution of 1-benzyl-4-benzyloxy-3-iodo-1H-pyridin-2-one (1.00 g, 2.40 mmol), diisopropylethylamine, (0.51 mL. 2.88 mmol) and Pd(dppf)2Cl2/CH2Cl2 (0.20 g, 0.24 mmol) in DMF (10.0 mL) was slowly added 1-phenyl-2-(triethylsilyl)acetylene (1.50 g, 7.20 mmol) at room temperature under N2. The resulting reaction mixture was degassed and stirred at 108° C. under nitrogen overnight. The reaction was cooled down to room temperature, and the solvent was removed. The residue was dissolved in DCM (250 mL). The solution was washed with NaHCO3 (30×2 mL) and brine (30 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography, eluting with ethyl acetate/methanol/100/1, to give the title compound. MS (m/z), M+H+ 416.2.

Workup

  1. customat room temperature
  2. customThe resulting reaction mixture
  3. customwas degassed
  4. temperatureThe reaction was cooled down to room temperature
  5. customthe solvent was removed
  6. dissolutionThe residue was dissolved in DCM (250 mL)
  7. washThe solution was washed with NaHCO3 (30×2 mL) and brine (30 mL)
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography
  11. washeluting with ethyl acetate/methanol/100/1

Sources & evidence

ORD record
ord-e64172fad13a46149b56e376ae601aee
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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