반응 #327361

반응 방정식

3-(1-methyl-1H-indol-5-yl)-phenylamine

DIEA

8-hydroxy-3-carboxy-coumarin

HATU

→

product

수율 48.0%

8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid [3-(1-methyl-1H-indol-5-yl)-phenyl]-amide

수율 48.0%

용매

DMF

반응 조건

후처리

1. 1
   기타resulted
2. 2
   기타to react overnight
3. 3
   기타DMF was removed under vacuum
4. 4
   기타The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage)
5. 5
   기타the fractions corresponding to the product peak were collected
6. 6
   기타the solvent removed under vacuum

실험 절차

DIEA (0.012 mL, 0.071 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.013 g, 0.065 mmol) and HATU (0.027 g, 0.071 mmol) in 0.5 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(1-methyl-1H-indol-5-yl)-phenylamine (0.014 g, 0.065 mmol) was added and allowed to react overnight. DMF was removed under vacuum and the reaction was resuspended in DMSO. The crude product was purified on a Parallex Flex parallel preparative reverse phase HPLC instrument (Biotage) using a solvent gradient of 10-95% ACN/H2O with 0.05% TFA at a flow rate of 20 mL/min. UV absorbance was monitored at 254 nm and the fractions corresponding to the product peak were collected and the solvent removed under vacuum to give 0.012 g of product in 48% yield: LCMS (ESI) m/z 411 (MH+).

출처