تفاعل #339714

معادلة التفاعل

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

المردود 90.0%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter addition
2. 2
   غسيلthe reaction mixture is washed with aqueous HCl solution
3. 3
   أخرىThe organic layer is dried
4. 4
   تركيزconcentrated
5. 5
   أخرىPurification by silica column (1:1 CH2Cl2/EtOAc)

الإجراء التجريبي

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.

المصدر