反応 #41996

反応方程式

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

triphenylphosphine

imidazole

iodine

→

title compound

収率 40.0%

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

収率 40.0%

溶媒

tetrahydrofuran

ether

反応条件

後処理

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

実験手順

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).

出典