反应 #41996

反应方程式

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

triphenylphosphine

imidazole

iodine

→

title compound

收率 40.0%

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

收率 40.0%

溶剂

tetrahydrofuran

ether

反应条件

后处理

1. 1
   workup.STIRRINGstir for 48 hours
2. 2
   洗涤wash with water (2×)
3. 3
   洗涤wash with 1N aqueous hydrochloric acid (2×)
4. 4
   干燥dry over anhydrous sodium sulfate
5. 5
   过滤filter
6. 6
   浓缩concentrate the solution
7. 7
   其他Purify the residue on silica eluting with 50 to 100% ethyl acetate/hexanes over 25 minutes

实验过程

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).

来源