Reaktion #359882

Reaktionsgleichung

4-iodo-2-methoxy benzoic acid

HATU

DIEA

HOBt

Acetamide oxime

→

desired product

Ausbeute 39.0%

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

Ausbeute 39.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereaction
2. 2
   workup.STIRRINGwas stirred for 30 minutes at room temperature
3. 3
   TemperaturThe reaction was then heated to 110° C. for 16 hours
4. 4
   TemperaturCooled to room temperature
5. 5
   SonstigePartitioned between ethyl acetate and water
6. 6
   WaschenThe organic layer was washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under vacuum
10. 10
    SonstigeThe residue was purified by HPLC

Vorschrift

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).

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