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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1698682Generated: October 25, 2026

Trimethylsilyl cyanide → (7-Methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

https://huagongshe.com/reaction/1698682

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylsilyl cyanideHCID 82115—
ReactantYtterbium triflateHCID 2733225—
Reactant4-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 18188176—
Reactant7-Methoxy-2,3-dihydrobenzofuran-5-carbaldehydeHCID 22343801—
SolventTetrahydrofuranHCID 8028—
Product(7-Methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrileHCID 67096962—

Reaction Steps

To a solution of 426 mg of Yb(OTf)3 in 30 ml of THF there were added 1.2 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1.22 g of 7-methoxy-2,3-dihydrobenzofuran-5-carbaldehyde [CAS No. 363185-46-0], 1 g of MS3A and 1.9 ml of trimethylsilyl cyanide under a nitrogen atmosphere, and the mixture was stirred at room temperature. The reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give a crude product of (7-methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163787B2
Source datasetuspto-grants-2012_04
ORD IDord-28499abc2f2e4b6ea070269fe5531b3f
Source noteuspto-grants-2012_04