반응 #41996

반응 방정식

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

triphenylphosphine

imidazole

iodine

→

title compound

수율 40.0%

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

수율 40.0%

용매

tetrahydrofuran

ether

반응 조건

후처리

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

실험 절차

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).

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