Water → HCID 68912754, compound

HRID 2096133Notes

Reaction equation

HRID 2096133 reaction equation
[CH2:1]([CH:8]1[N:13]([CH3:14])[C:12](=[O:15])[CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2I)[N:10]([CH3:24])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:1]([CH:8]1[N:13]([CH3:14])[C:12](=[O:15])[CH:11]([CH:16]([C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]([CH3:24])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 5062348DiisopropylamideHCID 68535478HCID 68535478, compound

Product 1

HCID 68912754HCID 68912754, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Under argon, 3-benzyl-6-(2-iodobenzyl)-1,4-dimethylpiperazine-2,5-dione (polar isomer from 1.5, 100 mg, 0.22 mmol) was stirred together with diisopropylamide (0.5 ml), trimethylsilylacetylene (40 mg, 0.4 mmol), Pd(PPh3)4 (60 mg, 0.05 mmol) and CuI (10 mg, 0.05 mmol) in DMF (abs., 5 ml) at 80° C. for 12 h. After cooling and addition of H2O, the mixture was extracted with methyl tert-butyl ether and the organic phases were dried and concentrated. Purification by column chromatography gave 21 mg (23%) of the target compound as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with methyl tert-butyl ether
  3. customthe organic phases were dried
  4. concentrationconcentrated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-f530ffc3ef6b4b75914ed0477ffae5fc
Source dataset
uspto-grants-2013_05
Patent number
US08450301B2

Reaction notes

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