Phenylacetylene → HCID 90390415, compound

HRID 2206867Notes

Reaction equation

HRID 2206867 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[C:11]2[N:12]([CH3:17])[O:13][C:14](=[O:16])[N:15]=2)[N:6]=1.[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28]C=CC=1>C1COCC1.[Cu](I)I>[CH:24]1([C:29]#[C:28][C:2]2[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)\[C:11]3[N:12]([CH3:17])[O:13][C:14](=[O:16])[N:15]=3)[N:6]=2)[CH2:30][CH2:31]1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 71627024HCID 71627024, compound

Product 1

HCID 90390415HCID 90390415, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (210 mg, 0.514 mmol, 1 eq) in degased THF (2 mL) was added in a microwave tube under argon tetrakis(triphenylphosphine)palladium (0) (59.4 mg, 0.051 mmol, 0.1 eq), copper iodide (14.6 mg, 0.077 mmol, 0.15 eq) N,N-diisopropylethylamine (0.358 ml, 2.06 mmol, 4 eq) and phenylacetylene (157 mg, 1.54 mmol, 3 eq). The mixture was stirred at room temperature for 2 days. The mixture was concentrated, diluted with ethyl acetate and filtered over a celite cartridge. The solvent was evaporated and the residue was purified by chromatography on silica gel to afford 3-[(Z)-({[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}imino)(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (148 mg, 73% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. filtrationfiltered over a celite cartridge
  4. customThe solvent was evaporated
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-002f25a205e643eaa8c26938b72696ac
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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