Réaction #1726696

Équation de réaction

4-Hydroxybenzaldehyde

cesium carbonate

4B

1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

→

9A

Rendement 62.1%

4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde

Rendement 62.1%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températurethen cooled to RT
2. 2
   FiltrationThe solids were filtered off
3. 3
   Autrethe filtrate was evaporated
4. 4
   workup.ADDITIONThe residue was treated with methanol
5. 5
   Autrethe solid formed
6. 6
   Filtrationwas collected by filtration
7. 7
   AutreDrying under vacuum

Mode opératoire

4-Hydroxybenzaldehyde (1.10 g, 9.17 mmol), cesium carbonate (3.49 g, 10.70 mmol) and 4B (2.70 g, 7.64 mmol) were mixed with DMF (80 mL). The mixture was stirred at 110° C. for 18 h then cooled to RT. The solids were filtered off and the filtrate was evaporated. The residue was treated with methanol and the solid formed was collected by filtration. Drying under vacuum gave 1.8 g (62%) of 9A as a beige solid. 1H NMR (500 MHz, DMSO-d6): δ 3.85 (s, 3H), 4.13 (dd, 1H), 4.57 (dd, 1H), 4.65 (dd, 1H), 5.12 (dd, 1H), 5.29 (m, 1H), 7.10 (d, 2H), 7.16 (d, 2H), 7.90 (d, 2H), 8.00 (d, 2H), 9.90 (s, 1H), MS (APCI+) m/z 380 [M+H]+.

Source