Reaction #359882

Reaction equation

4-iodo-2-methoxy benzoic acid

HATU

DIEA

HOBt

Acetamide oxime

→

desired product

Yield 39.0%

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

Yield 39.0%

Solvents

DMF

Conditions

Workup

1. 1
   Otherreaction
2. 2
   workup.STIRRINGwas stirred for 30 minutes at room temperature
3. 3
   TemperatureThe reaction was then heated to 110° C. for 16 hours
4. 4
   TemperatureCooled to room temperature
5. 5
   OtherPartitioned between ethyl acetate and water
6. 6
   WashThe organic layer was washed with brine
7. 7
   Dryingdried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under vacuum
10. 10
    OtherThe residue was purified by HPLC

Procedure

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