Réaction #2186207

Équation de réaction

piperidine

4-[(2-Fluoro-ethyl)-methyl-amino]-2-hydroxy-benzaldehyde

(5-thiophen-2-yl-[1,3,4]oxadiazol-2-yl)-acetic acid methyl ester

→

desired product

Rendement 19.0%

7-[(2-Fluoro-ethyl)-methyl-amino]-3-(5-thiophene-2-yl-[1,3,4]oxadiazol-2-yl)-chromen-2-one

Rendement 19.0%

Solvants

acetonitrile

benzene

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureto reflux for 1 h
3. 3
   Autreto reach room temperature
4. 4
   Autreevaporated
5. 5
   Autrethe residue column chromatographed (silica gel, AcOEt/petroleum ether 1:1)
6. 6
   AutreThe fluorescent, yellow product is triturated in diisopropylether
7. 7
   Autredried under high vacuum

Mode opératoire

40 mg (ca. 0.2 mmol) crude 4-[(2-Fluoro-ethyl)-methyl-amino]-2-hydroxy-benzaldehyde and 30 mg (0.13 mmol) (5-thiophen-2-yl-[1,3,4]oxadiazol-2-yl)-acetic acid methyl ester are dissolved under argon in 4 mL benzene and 2 mL acetonitrile, treated with 0.03 mL (2 eq.) piperidine and heated to reflux for 1 h. The reaction mixture is allowed to reach room temperature, evaporated, and the residue column chromatographed (silica gel, AcOEt/petroleum ether 1:1). The fluorescent, yellow product is triturated in diisopropylether, then dried under high vacuum to yield 9 mg (19%) desired product as a yellow powder.

Source