Diisopropylethylamine → Ammonia

Participants

Reaction Steps

A mixture of (R)—N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide.trifluoroacetate (40 mg, 0.091 mmol), (R)-(+)-3-chlorostyrene oxide (24 μL, 0.18 mmol) and iPr2NEt (24 μL, 0.137 mmol) in acetonitrile (1 mL) is refluxed for 8 hours. After cooling, the mixture is concentrated and purified by preparative TLC (thickness: 0.5 mm, methanol/(a saturated ammonia solution in chloroform)=1/3) and preparative reversed phase HPLC (trifluoroacetic acid/water/acetonitrile) to give the desired N-[2-(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indol-7-yloxy)acetyl]methanesulfonamide.trifluoroacetate (9 mg, yield: 21%).

Provenance & Evidence