تفاعل #41996

معادلة التفاعل

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

triphenylphosphine

imidazole

iodine

→

title compound

المردود 40.0%

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

المردود 40.0%

المذيبات

tetrahydrofuran

ether

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر