Reacción #41996

Ecuación de reacción

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

triphenylphosphine

imidazole

iodine

→

title compound

Rendimiento 40.0%

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

Rendimiento 40.0%

Disolventes

tetrahydrofuran

ether

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente