Water → HCID 53839973, compound

HRID 2268871Notes

Reaction equation

HRID 2268871 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.[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([C:29]#[C:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][N:7]=[CH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 54160016HCID 54160016, compound

Product 1

HCID 53839973HCID 53839973, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture under N2 of trifluoro-methanesulfonic acid 6-methoxy-1-oxo-1,2-dihydro-phthalazin-5-yl ester (1 g, 3.08 mmoles), prepared as described in example 59, phenylacetylene (0.507 ml, 4.62 mmoles), bis(triphenylphosphine)PdCl2 (108 mg, 0.154 mmole), triethylamine (1.71 ml, 12.32 mmoles) in DMF (20 ml) was heated at 90° C. under stirring for 3 hours, then cooled, poured into water and extracted with CH2Cl2. The extract was washed with water, anhydrified over Na2SO4 and brought to dryness. The residue was taken up in ethyl ether and filtered to give 680 mg of the title compound (yield: 80%).

Workup

  1. temperaturecooled
  2. extractionextracted with CH2Cl2
  3. washThe extract was washed with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4bac543b44df4cafb052908f04c81252
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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