Réaction #359882

Équation de réaction

4-iodo-2-methoxy benzoic acid

HATU

DIEA

HOBt

Acetamide oxime

→

desired product

Rendement 39.0%

5-(4-iodo-2-methoxyphenyl)-3-methyl-1,2,4-oxadiazole

Rendement 39.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrereaction
2. 2
   workup.STIRRINGwas stirred for 30 minutes at room temperature
3. 3
   TempératureThe reaction was then heated to 110° C. for 16 hours
4. 4
   TempératureCooled to room temperature
5. 5
   AutrePartitioned between ethyl acetate and water
6. 6
   LavageThe organic layer was washed with brine
7. 7
   Séchagedried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under vacuum
10. 10
    AutreThe residue was purified by HPLC

Mode opératoire

A mixture of 4-iodo-2-methoxy benzoic acid (83 mg, 0.3 mmol), HATU (114 mg, 0.3 mmol), DIEA (26 μL, 0.15 mmol), and HOBt (8 mg, 0.06 mmol) in DMF was stirred at room temperature for 5 minutes. Acetamide oxime (22 mg, 0.3 mmol) was added, and reaction was stirred for 30 minutes at room temperature. The reaction was then heated to 110° C. for 16 hours. Cooled to room temperature. Partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by HPLC to provide 37 mg (39%) of desired product. MS (ESI) m/e 317 (M+H)+, 1H NMR (300 MHz, DMSO-d6): □ 7.70 (d, J=8.14 Hz, 1H), 7.64 (d, J=1.36 Hz, 1H), 7.53 (dd, J=8.31-1.53 Hz, 1H), 3.94 (s, 3H), 2.40 (s, 3H).

Source