Reaktion #2166327

Reaktionsgleichung

4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine

8-methoxychromane-6-carbaldehyde

1g

2-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid trifluoroacetate

trimethylsilyl cyanide

Yb(OTf)3

→

(8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through celite
2. 2
   Waschenthe celite was washed with 100 ml of ethyl acetate
3. 3
   EinengenThe organic layer was concentrated under reduced pressure

Vorschrift

After adding 700 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 770 mg of 8-methoxychromane-6-carbaldehyde [CAS No. 81258-23-3], 1g of MS3A and 1.1 ml of trimethylsilyl cyanide to a solution of 250 mg of Yb(OTf)3 in 5 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred overnight 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 (8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile.

Quelle