Реакция #41996

Уравнение реакции

N-{3-[5-Fluoro-1-(3-hydroxy-propyl)-indan-1-yl]-1H-indol-7-yl}-methanesulfonamide

triphenylphosphine

imidazole

iodine

→

title compound

Выход 40.0%

N-{3-[5-Fluoro-1-(3-iodo-propyl)-indan-1-yl]-1H-indol-7-yl}-methanesulfonamide

Выход 40.0%

Растворители

tetrahydrofuran

ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGstir for 48 hours
2. 2
   Промывкаwash with water (2×)
3. 3
   Промывкаwash with 1N aqueous hydrochloric acid (2×)
4. 4
   Сушкаdry over anhydrous sodium sulfate
5. 5
   Фильтрацияfilter
6. 6
   Концентрированиеconcentrate the solution
7. 7
   ДругоеPurify the residue on silica eluting with 50 to 100% ethyl acetate/hexanes over 25 minutes

Методика

To a solution of triphenylphosphine (422 mg, 1.61 min ol, 1.30 equivalents) and imidazole (219 mg, 3.22 mmol, 2.60 equivalents) in anhydrous tetrahydrofuran (10 ml) add iodine (410 mg, 1.61 mmol, 1.30 equivalents). After stirring for 20 minutes at room temperature under nitrogen, add N-{3-[5-Fluoro-1-(3-hydroxy-propyl)-indan-1-yl]-1H-indol-7-yl}-methanesulfonamide (500 mg, 1.24 mmol) and stir for 48 hours. Dilute with ether, wash with water (2×), wash with 1N aqueous hydrochloric acid (2×), dry over anhydrous sodium sulfate, filter, and concentrate the solution. Purify the residue on silica eluting with 50 to 100% ethyl acetate/hexanes over 25 minutes to obtain the title compound as a white solid (254 mg, 40%). LC-MS m/z 385.0 (M+−I).

Источник