반응 #593246

반응 방정식

methansulfonyl chloride

2-[4-(2-Aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile

Methanesulfonyl chloride

→

N-{2-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)phenoxy]ethyl}methanesulfonamide

용매

pyridine

반응 조건

후처리

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITcontinues for another hour
3. 3
   기타The reaction mixture is partitioned between EtOAc and aqueous HCl
4. 4
   기타The organic layer is dried
5. 5
   농축concentrated
6. 6
   기타Purification by silica gel chromatography (1/1 CH2Cl2/EtOAc)

실험 절차

2-[4-(2-Aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (30 mg, 0.09 mmol), prepared in step B, above, is dissolved in pyridine (300 μL). Methanesulfonyl chloride (8 μL, 0.1 mmol) is added. This is stirred at room temperature for 45 minutes. More methansulfonyl chloride (4 μL, 0.05 mmol) is added. Stirring continues for another hour. The reaction mixture is partitioned between EtOAc and aqueous HCl. The organic layer is dried and concentrated. Purification by silica gel chromatography (1/1 CH2Cl2/EtOAc) yields N-{2-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)phenoxy]ethyl}methanesulfonamide, compound 268 (32 mg, 86%) as a white solid.

출처