Reaction #41996

Reaction equation

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

triphenylphosphine

imidazole

iodine

→

title compound

Yield 40.0%

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

Yield 40.0%

Solvents

tetrahydrofuran

ether

Conditions

Workup

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

Procedure

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).

Source