Trimethylsilylacetylene → HCID 66577713, compound

HRID 1183357Notes

Reaction equation

HRID 1183357 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Zn]CC)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[C:20]=2/[CH:25]=[N:26]/[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[C:20]=2[CH:25]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 87057700HCID 87057700, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 66577713HCID 66577713, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(Trimethylsilyl)acetylene (0.6926 mL, 5 mmol) and diethylzinc (1.1M in toluene, 4.54 mL, 5 mmol) were dissolved in toluene (15.5 mL) and stirred for 1 hour at room temperature. Then, N-[1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-meth-(E)-ylidene]-methanesulfonamide (1 g, 0.291 mmol) was added and the reaction was heated to 60° C. for 20 hours. The reaction was quenched with H2O and submitted to aqueous workup then purified via silica gel chromatography to yield the title compound which was brought directly to the next step.

Workup

  1. temperaturethe reaction was heated to 60° C. for 20 hours
  2. customThe reaction was quenched with H2O
  3. customthen purified via silica gel chromatography

Sources & evidence

ORD record
ord-a5e55f0623994ca5995893e809232be4
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

Loading…