HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 4-[3-Hydroxy-4-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-butyl]-6-methoxy-1H-indole-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene | HCID 59686818 | — |
| Reactant | 6-Methoxy-4-(2-oxiranyl-ethyl)-1H-indole-2-carboxylic acid methyl ester | HCID 86619151 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[3-Hydroxy-4-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-butyl]-6-methoxy-1H-indole-2-carboxylic acid methyl ester | HCID 69233753 | — |
Reaction Steps
6-Methoxy-4-(2-oxiranyl-ethyl)-1H-indole-2-carboxylic acid methyl ester (120 mg, 0.43 mmol), Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (114 mg, 0.43 mmol), DIPEA (0.2 mL, 1.13 mmol), ethanol (3 mL), dichloromethane (2 mL) were heated for 1200 sec. at 130° C. in a μW reaction tube. The solvent was evaporated under reduced pressure to yield a crude solid which was then purified with flash chromatography gradient [20% Ethyl acetate/heptane to 100% Ethyl acetate] to yield the title compound as a residue.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08530475B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-900ab4f2d20f402eadc80f38d5192c8a |
| Source note | uspto-grants-2013_09 |