Potassium Phosphate, Tribasic → (E)-7,8-dichloro-5-(2-(4-fluorophenyl)prop-1-enyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

7,8-Dichloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (900 mg, 3.54 mmol) was dissolved in DMF (5 mL). Copper (I) iodide (66 mg, 0.354 mmol), L-proline (81 mg, 0.69 mmol) and potassium phosphate (1.5 g, 7.08 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 1-(2-Bromovinyl)-4-fluorobenzene (900 mg, 4.23 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 80° C. (prolonged heating in some cases was required). DMF was evaporated under reduced pressure, the residue was diluted with water and the solid was filtered. The solid material was purified by silica gel chromatography (100-200 mesh) eluting with 0-10% MeOH-DCM. The product was further purified by HPLC.

1. customthe reaction mixture was purged with nitrogen
2. temperatureThe reaction mixture was heated overnight at 80° C. (
3. temperatureprolonged heating in some cases
4. customDMF was evaporated under reduced pressure
5. additionthe residue was diluted with water
6. filtrationthe solid was filtered
7. customThe solid material was purified by silica gel chromatography (100-200 mesh)
8. washeluting with 0-10% MeOH-DCM
9. customThe product was further purified by HPLC

ORDレコード

ord-a649abd69eca48b484b6c71d8f12b8d7

出典データセット

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08906925B2