Tetrahydrofuran → 3-{3-(4-nitrophenyl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-1-yl}-1-propanol

To a solution of 0.5M 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (6.16 mL) cooled to 0° C. was added a solution of 4-[3-(4-nitrophenyl)-1-(2-propen-1-yl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.06 mmol) in tetrahydrofuran (14 mL). The reaction mixture was stirred at room temperature under an inert atmosphere for 4.5 h and then re-cooled to 0° C. followed by quenching with water (1.7 mL). After 15 minutes of stirring at 0° C., 6N aqueous sodium hydroxide (1.24 mL) was added dropwise followed by 30% aqueous hydrogen peroxide (0.865 mL). The reaction mixture was stirred for 1.5 h at 0° C., neutralized with 6N aqueous hydrochloric acid and concentrated in vacuo. Water (10 mL) was added to the residue and the solution extracted with ethyl acetate (3×15 mL), the combined organic layers dried over magnesium sulfate and concentrated in vacuo to afford the title compound (84%). ESMS [M+H]+: 504.2

1. temperaturere-cooled to 0° C.
2. customby quenching with water (1.7 mL)
3. stirringAfter 15 minutes of stirring at 0° C.
4. addition6N aqueous sodium hydroxide (1.24 mL) was added dropwise
5. stirringThe reaction mixture was stirred for 1.5 h at 0° C.
6. concentrationconcentrated in vacuo
7. additionWater (10 mL) was added to the residue
8. extractionthe solution extracted with ethyl acetate (3×15 mL)
9. dry with materialthe combined organic layers dried over magnesium sulfate
10. concentrationconcentrated in vacuo

ORD 기록

ord-0efd3a38a7d34885bc3f8c1e0ccd7c37

출처 데이터셋

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07419988B2