반응 #339714

반응 방정식

morpholine

4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-benzoic acid

DMF

Oxalyl chloride

→

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

수율 90.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   세척the reaction mixture is washed with aqueous HCl solution
3. 3
   기타The organic layer is dried
4. 4
   농축concentrated
5. 5
   기타Purification by silica column (1:1 CH2Cl2/EtOAc)

실험 절차

4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-benzoic acid (50 mg, 0.16 mmol) is suspended in CH2Cl2 (2.2 mL) and catalytic DMF (2 μL). Oxalyl chloride (22 μL, 0.25 mmol) is added. The reaction mixture is stirred at room temperature for 1 hour, at which time full dissolution occurred. This reaction mixture is pipetted dropwise into a vigorously stirring solution of morpholine (1.0 mL) in CH2Cl2 (5 ml). After addition is complete, the reaction mixture is washed with aqueous HCl solution. The organic layer is dried and concentrated. Purification by silica column (1:1 CH2Cl2/EtOAc) yields 1-ethyl-6-methoxy-2-[4-(morpholine-4-carbonyl)-phenyl]-1H-indole-3-carbonitrile (56 mg, 90%) as a white solid.

출처