HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1) | HCID 2734203 | — |
| Reactant | Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate | HCID 14980577 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate | HCID 19097505 | — |
Reaction Steps
A solution of methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (Preparation 2) (25 g), 4-chloromethyl-2-methylthiazole hydrochloride (Maybridge Chemical Co., Ltd.) (11.6 g) and Cs2CO3 (68.7 g) in 250 mL of CH3CN were heated at reflux for 24 hours. The mixture was cooled, poured onto water, and extracted (2× EtOAc), washed twice with brine, dried (MgSo4), and evaporated. Chromatography of the residue on silica gel eluting with hexane/EtOAc 4:1 afforded the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05290798 |
| Source dataset | uspto-grants-1994_03 |
| ORD ID | ord-0f741723648b47b78d6eebd137cf3032 |
| Source note | uspto-grants-1994_03 |