Phenylacetylene → HCID 118624439, compound

HRID 2206864Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)\[C:12]2[N:13]([CH3:18])[O:14][C:15](=[O:17])[N:16]=2)[CH:5]=[CH:4][CH:3]=1.[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.[Cu](I)I>[CH3:18][N:13]1[C:12](/[C:11](/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:10]\[O:9][CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:32]#[C:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:7]=2)=[N:16][C:15](=[O:17])[O:14]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-[(Z)-{[(6-bromopyridin-2-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (200 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 heated in the microwave at 120° C. for 15 min. 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 2-methyl-3-[(Z)-phenyl({[6-(phenylethynyl)pyridin-2-yl]methoxy}imino)methyl]-1,2,4-oxadiazol-5(2H)-one (115 mg, 52% yield).

Workup

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

Sources & evidence

ORD record: ord-e7a0d930a3de46feb9f770fc10f20f0e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375010B2

Reaction notes

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