Water → HCID 18381656, compound

HRID 2268875Notes

Reaction equation

HRID 2268875 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.[CH2:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:23][CH2:24][C:25]#[CH:26].C(N(CC)CC)C.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([C:26]#[C:25][CH2:24][CH2:23][CH2:22][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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 745735-Phenyl-1-pentyneHCID 54160016HCID 54160016, compound

Product 1

HCID 18381656HCID 18381656, compoundYield 65.3%

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 (2 g, 6.16 mmoles), prepared as described in example 59, pent-4-ynyl-benzene (1.33 g, 9.24 mmoles), bis(triphenylphosphine)PdCl2 (216 mg, 0.308 mmole) and triethylamine (3.42 ml, 24.64 mmoles) in DMF (40 ml) was heated to 90° C. for 3 hours, then poured into water (200 ml), filtered and the precipitate was washed with water to give 1.28 g of the title compound (yield: 65%).

Workup

  1. filtrationfiltered
  2. washthe precipitate was washed with water

Sources & evidence

ORD record
ord-240bc892e5ca4ec78469a233c2e5d288
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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