Dimethyl Sulfoxide → methyl 1-allyl-3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate

Temperatur

-78 °C

DMSO (5 eq.) was dissolved in DCM and the solution was cooled to −78° C. To the stirred solution oxalylchloride (2.5 eq.) was added and the mixture was left stirring for 30 min. A solution of methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate (1 eq.) in DCM (0.25M solution) was added and the mixture was left stirring for 30 min at −78° C. Et3N (8 eq.) was added and the mixture was allowed to warm to 0° C. At this temperature stirring was continued for 2 h, and then stirring was continued at RT overnight. The mixture was diluted with DCM, and then washed with water, 1N HCl, saturated aq. NaHCO3 solution and with brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residual material was purified by flash chromatography (PE:EtOAc, 9:1). After evaporation of the solvents the product was obtained as a yellow foam (88%). MS (ES+): 432.1 (M+H+).

1. waitthe mixture was left
2. waitthe mixture was left
3. stirringstirring for 30 min at −78° C
4. temperatureto warm to 0° C
5. stirringAt this temperature stirring
6. waitwas continued for 2 h
7. stirringstirring
8. waitwas continued at RT overnight
9. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and with brine
10. dry with materialAfter drying over Na2SO4 all volatiles
11. customwere evaporated in vacuo
12. customThe residual material was purified by flash chromatography (PE:EtOAc, 9:1)
13. customAfter evaporation of the solvents the product

ORD-Eintrag

ord-ee30a91f0d7d42a9a9762bdc2d6de347

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08232390B2