Sodium hydride → 5-Allyloxy-1-[(6-chlorobenzo[1,3]dioxol-5-yl)methyl]-1h-indole-2-carboxylic acid ethyl ester

To a mixture of NaH (60% suspension in mineral oil, 0.24 g, 6.12 mmol) and DMF (20 mL) was added 5-allyloxyindole-2-carboxylic acid ethyl ester (1.0 g, 4.08 mmol), from Example 1(d). After stirring at room temperature for 1 h, 6-chloropiperonyl chloride (0.84 g, 4.08 mmol) was added followed by the addition of tetrabutyl ammonium iodide (0.15 g, 0.41 mmol). The reaction was stirred at room temperature for 18 h. When the reaction was complete as indicated by TLC, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed in vacuo and the resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes) to yield the desired product as an oil (0.72 g, 43%). LC/MS (ES+) m/e 414.0 [M+H]+.

1. stirringThe reaction was stirred at room temperature for 18 h
2. customthe reaction mixture was partitioned between EtOAc and water
3. washThe organic layer was washed with brine
4. dry with materialdried (Na2SO4)
5. customThe solvent was removed in vacuo
6. customthe resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes)

ORD 기록

ord-b1232f5cd63a4771b76d4c4fa67413d4

출처 데이터셋

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06670388B1