Reacción #90780

Ecuación de reacción

2,5-dichloro-4-iodo-pyridine

2-amino-N-methoxy-benzamide

K3PO4

→

title compound

Rendimiento 87.5%

2-(2,5-Dichloropyridin-4-ylamino)-N-methoxy-benzamide

Rendimiento 87.5%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed with N2 for 1 h
2. 2
   Otroagain degassed for 15 min with N2
3. 3
   OtroAfter completion of reaction, solid material
4. 4
   Filtraciónwas collected by filtration
5. 5
   workup.DISSOLUTIONdissolved in water (500 mL)
6. 6
   Extracciónextracted with ethyl acetate (5×200 mL)
7. 7
   SecadoCombined organic layer was dried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroSolid compound so obtained
11. 11
    Otrowas purified
12. 12
    Lavadoby washing with hexane

Procedimiento

A mixture of 2,5-dichloro-4-iodo-pyridine (40 g, 146.5 mmole, 1 eq), 2-amino-N-methoxy-benzamide (24.32 g, 146.5 mmole, 1 eq) and K3PO4 (77.72 g 366.2 mmole, 2.5 eq) in 1,4-dioxane (600 mL) was degassed with N2 for 1 h. To this were added Pd(OAc)2 (0.657 g, 2.93 mmole, 0.02 eq), DPEPhos (6.31 g, 11.7 mmole, 0.08 eq) and again degassed for 15 min with N2. The resulting mixture was stirred at 110° C. for overnight. After completion of reaction, solid material was collected by filtration, dissolved in water (500 mL) and extracted with ethyl acetate (5×200 mL). Combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Solid compound so obtained was purified by washing with hexane to give the title compound as yellowish solid (40 g, 53%). 1H-NMR (400 MHz, DMSO-d6): δ 3.63 (s, 3H), 7.06 (s, 1H), 7.15-7.22 (m, 1H), 7.48-7.57 (m, 2H), 7.66-7.67 (d, 1H, J=7.48 Hz), 8.25 (s, 1H), 10.66-11.45 (brs, 1H). LC-MS [M+H]+=312.3.

Fuente