반응 #817483

반응 방정식

N2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-pyridine-2,4-diamine

potassium iodide

iodine

→

title compound

(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-iodo-pyridin-2-yl)-amine

용매

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   기타the insoluble materials were removed by filtration
3. 3
   workup.ADDITIONthe filtrate was diluted with EtOAc
4. 4
   세척washed with 25% aqueous NH4OH, 5% aqueous sodium bisulfite
5. 5
   기타The organic layer was separated
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified on a Biotage 40 M column (2.5:1 hexane:EtOAc)

실험 절차

Isopentyl nitrile (Aldrich Chemical Company) (3.9 mL, 29 mmol) was added to a mixture of N2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-pyridine-2,4-diamine (Example 2(a), 2.4 g, 9.8 mmol), potassium iodide (Aldrich Chemical Company) (1.6 g, 9.8 mmol), iodine (Aldrich Chemical Company) (1.2 g, 4.9 mmol) and copper (I) iodide (Aldrich Chemical Company) (1.9 g, 9.8 mmol) in 1,2-dimethoxyethane (60 mL). The reaction mixture was heated at 60-65° C. for 1 hr. After cooling to room temperature, the insoluble materials were removed by filtration and the filtrate was diluted with EtOAc, washed with 25% aqueous NH4OH, 5% aqueous sodium bisulfite and then brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified on a Biotage 40 M column (2.5:1 hexane:EtOAc) to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 355 (M+1).

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