Reaction #41998

Reaction equation

N-{3-[5-fluoro-1-(3-iodo-propyl)-indan-1-yl]-1H-indol-7-yl}-methane sulfonamide

morpholine

→

title compound

Yield 83.0%

N-{3-[5-Fluoro-1-(3-morpholin-4-yl-propyl)-indan-1-yl]-1H-indol-7-yl}-methanesulfonamide

Yield 83.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   OtherRemove the volatiles under high vacuum
2. 2
   workup.DISSOLUTIONdissolve the residue in dichloromethane
3. 3
   workup.ADDITIONadd solid potassium carbonate
4. 4
   Filtrationfilter
5. 5
   Concentrationconcentrate in vacuo
6. 6
   OtherPurify the residue on silica eluting with 5 to 10% methanol in dichloromethane over 15 minutes

Procedure

Combine N-{3-[5-fluoro-1-(3-iodo-propyl)-indan-1-yl]-1H-indol-7-yl}-methane sulfonamide (65 mg, 0.13 mmol) and morpholine (2 ml) in anhydrous tetrahydrofuran (2.5 ml) and stir at room temperature under nitrogen overnight. Remove the volatiles under high vacuum, dissolve the residue in dichloromethane, add solid potassium carbonate, stir for ten minutes, filter, and concentrate in vacuo. Purify the residue on silica eluting with 5 to 10% methanol in dichloromethane over 15 minutes to obtain the title compound as a white solid (50 mg, 83%). LC-MS m/z 472.2 (M++1).

Source