Triethylamine → HCID 18381612, compound

HRID 2268933Notes

Reaction equation

HRID 2268933 reaction equation
[CH3:1][O:2][C:3]1[C:4](OS(C(F)(F)F)(=O)=O)=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][N:7]=[CH:6]2.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24].C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][N:7]=[CH:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2×HCID 54160016HCID 54160016, compound

Product 1

HCID 18381612HCID 18381612, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of trifluoromethanesulfonic acid 6-methoxy-1-oxo-1,2-dihydro-phthalazin-5-yl ester (4.52 g, 13.94 mmoles), prepared as described in example 59, trimethylsilylethyne (3.94 ml, 27.88 mmoles), bis(triphenylphosphine)PdCl2 (245 mg, 0.384 mmole) and triethylamine (6.56 ml) in DMF (30 ml) was heated at 60° C. for 4 hours. Further trimethylsilylethyne (2 ml) was added and the mixture was heated at 90° C. for 3 hours. After evaporation of the solvent, the residue was taken up in ethyl acetate and the solid was filtered off. After evaporation, the residue was taken up in diethylcarbonate, washed with water, dried, evaporated again, taken up in ethyl ether and filtered giving 2.87 g of the title compound (yield: 75.6%).

Workup

  1. temperaturethe mixture was heated at 90° C. for 3 hours
  2. customAfter evaporation of the solvent
  3. filtrationthe solid was filtered off
  4. customAfter evaporation
  5. washwashed with water
  6. customdried
  7. customevaporated again
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6f519798cb6f4f75bf9b584d31ca0348
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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