Reaction #2328985

Reaction equation

6-Chloro-N-(2-hydroxy-4-methoxyphenyl)nicotinamide

DMF

water

→

title compound

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine

Conditions

Workup

1. 1
   Otherthe solid was collected
2. 2
   Washrinsed with water
3. 3
   Otherdried
4. 4
   OtherThe crude product was purified by flash column chromatography

Procedure

6-Chloro-N-(2-hydroxy-4-methoxyphenyl)nicotinamide (40 mg, 0.14 mmol) was dissolved in DMF (1.5 mL) and one drop of sulfuric acid was added. The reaction was run at 230° C. for 20 minutes in a microwave reactor. The mixture was added to water, the solid was collected, rinsed with water and dried. The crude product was purified by flash column chromatography using 40% ethyl acetate in hexane, giving the title compound (14 mg) as an orange solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.96 (d, 1H) 8.19 (dd, 1 H) 7.57 (d, 1H) 7.10 (d, 1H) 6.92 (dd, 1H) 6.60 (d, 1H) 3.88 (s, 3H) 3.20 (s, 6H); MS m/z (M+H) 270.

Source