HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl 3-chloro-2-oxopentanoate → 2-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-5-ethyl-thiazole-4-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 3-chloro-2-oxopentanoate | HCID 13719444 | — |
| Reactant | 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbothioic acid amide | HCID 86073268 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-5-ethyl-thiazole-4-carboxylic acid ethyl ester | HCID 68694920 | 152.3% |
Reaction Steps
A mixture of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbothioic acid amide (0.227 g, 0.754 mmol) and crude 3-chloro-2-oxo-pentanoic acid ethyl ester (1.34 g, 7.52 mmol) in dimethylformamide (4 ml) was subjected to microwave irradiation for 25 min at 140° C. The reaction mixture was concentrated in vacuo and the obtained reside was purified by silica gel column chromatography eluting with 25% acetone in heptane to afford crude 2-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-5-ethyl-thiazole-4-carboxylic acid ethyl ester (0.490 g). This material was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700634B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-afc903a5336744a697ca743d7acd9aec |
| Source note | uspto-grants-2010_04 |