反応 #90780

反応方程式

2,5-dichloro-4-iodo-pyridine

2-amino-N-methoxy-benzamide

K3PO4

→

title compound

収率 87.5%

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

収率 87.5%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他was degassed with N2 for 1 h
2. 2
   その他again degassed for 15 min with N2
3. 3
   その他After completion of reaction, solid material
4. 4
   ろ過was collected by filtration
5. 5
   workup.DISSOLUTIONdissolved in water (500 mL)
6. 6
   抽出extracted with ethyl acetate (5×200 mL)
7. 7
   乾燥Combined organic layer was dried over sodium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他Solid compound so obtained
11. 11
    その他was purified
12. 12
    洗浄by washing with hexane

実験手順

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.

出典