Реакция #90780

Уравнение реакции

2,5-dichloro-4-iodo-pyridine

2-amino-N-methoxy-benzamide

K3PO4

→

title compound

Выход 87.5%

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

Выход 87.5%

Растворители

1,4-dioxane

Условия реакции

Обработка

1. 1
   Другоеwas degassed with N2 for 1 h
2. 2
   Другоеagain degassed for 15 min with N2
3. 3
   ДругоеAfter completion of reaction, solid material
4. 4
   Фильтрацияwas collected by filtration
5. 5
   workup.DISSOLUTIONdissolved in water (500 mL)
6. 6
   Экстракцияextracted with ethyl acetate (5×200 mL)
7. 7
   СушкаCombined organic layer was dried over sodium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеSolid compound so obtained
11. 11
    Другоеwas purified
12. 12
    Промывкаby washing with hexane

Методика

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.

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