Dimethylformamide → 4-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole

温度

23 °C

In a round bottom flask was added 4-iodopyrazole (10.22 g, 52.70 mmol), Cs2CO3 (20.6 g, 63.2 mmol), and anhydrous DMF (100 mL). The suspension was stirred at 23° C. for 5 min. 2-(2-bromoethoxy)tetrahydro-2H pyran (9.95 mL, 63.2 mmol) was added and the reaction was stirred at 70° C. for 16 hours. After cooling down, EtOAc (100 mL) and water (100 mL) was added to the reaction. The organic layer was collected, and the aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with water (3×100 mL), dried over Na2SO4, and concentrated to afford dark brown oil. The crude product was purified on a silica gel column eluting with ethyl acetate and hexanes to provide 4-iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole as yellow oil (14.78 g, 87% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.89 (s, 1H) 7.52 (s, 1H) 4.47-4.56 (m, 1H) 4.25-4.35 (m, 2H) 3.81-3.96 (m, 1H) 3.66-3.75 (m, 1H) 3.45-3.57 (m, J=2.83 Hz, 1H) 3.32-3.40 (m, 1H) 1.34-1.71 (m, 6H).

1. stirringthe reaction was stirred at 70° C. for 16 hours
2. temperatureAfter cooling down
3. customThe organic layer was collected
4. extractionthe aqueous layer was extracted with EtOAc (3×100 mL)
5. washThe combined organic layers were washed with water (3×100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customto afford dark brown oil
9. customThe crude product was purified on a silica gel column
10. washeluting with ethyl acetate and hexanes

ORDレコード

ord-c6f381056eac4b11b356f65efc6d58ea

出典データセット

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07732604B2