Water → HCID 69997151, compound

HRID 963430Notes

Reaction equation

HRID 963430 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:2].C([Si:22]([CH3:25])([CH3:24])[CH3:23])#C.O.[CH2:27](N(CC)CC)[CH3:28]>CN(C)C=O.[Cu]I>[CH2:27]([C:2]#[C:1][N:3]1[C:12]2[C:7](=[CH:8][C:9]([Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 619729HCID 619729, compound

Product 1

HCID 69997151HCID 69997151, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 1-ethyl-6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 13h)), 1.94 ml of ethynyltrimethylsilane, 70 mg of bis-trimethylphosphine-palladium dichloride and 2.5 mg of copper(I) iodide in 7 ml of triethylamine and 7 ml of dimethylformamide is stirred at 60° for 9 hrs. After cooling to room temperature the reaction mixture is treated with 100 ml of water and extracted twice with 50 ml of methylene chloride each time. The combined organic phases are washed twice with 250 ml of water each time and once with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate. The crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1. 1.27 g (80%) of ethyl 1-ethyl-6-trimethylsilyl-ethynyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate are obtained.

Workup

  1. extractionextracted twice with 50 ml of methylene chloride each time
  2. washThe combined organic phases are washed twice with 250 ml of water each time
  3. dry with materialonce with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate
  4. customThe crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-b05545c695d14780a152db0bc7a6d2c2
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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