反应详情

5-Methoxy-1 h-pyrrolo[3,2-b]pyridine-2-carboxylic acid (0.602 mmol, 116 mg) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.662 mmol, 252 mg) were added to a solution of 4-amino-3-methoxyphenylboronic acid pinacol ester (0.602 mmol, 150 mg) in dichloromethane (2.5 ml) and pyridine (0.5 ml) at 0° C. After stirring the reaction mixture overnight at room temperature it was concentrated in vacuo. Dichloromethane and water were added to the residue, the organic layer separated and washed with water. Both aqueous layers were extracted with dichloromethane. The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane) to give 5-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxamide (278 mg).

1. concentrationwas concentrated in vacuo
2. additionDichloromethane and water were added to the residue
3. customthe organic layer separated
4. washwashed with water
5. extractionBoth aqueous layers were extracted with dichloromethane
6. dry with materialThe combined organic layers were dried (sodium sulfate)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography (silica gel, dichloromethane)