HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Methyl 3-[1-(4-Chlorobenzyl)-5-(furo[3,2-b]pyridin-5-ylmethoxy) indol-2-yl]-2,2-dimethylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate | HCID 14980565 | — |
| Reactant | 5-(Bromomethyl)furo[3,2-b]pyridine | HCID 18950579 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 3-[1-(4-Chlorobenzyl)-5-(furo[3,2-b]pyridin-5-ylmethoxy) indol-2-yl]-2,2-dimethylpropanoate | HCID 23202372 | — |
Reaction Steps
A solution of 440 mg(1.18 mmol) of methyl 3-[1-(4-chlorobenzyl) -5-hydroxyindol-2-yl]-2,2-dimethylpropanoate, 5(bromomethyl)furo[3,2-b]pyridine (274 mg (1.3 mmol) from Step 3), and 772 mg (2.4 mmol) of Cs2CO3 in 6 mL of acetonitrile was stirred at r.t. for 18 hr. The reaction was diluted with aqueous NH4OAc 25% w/v (50 mL) and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The resulting residue was purified by chromatography on silica gel eluted with 25-30 % EtOAc in hexane to give the title compound as a colorless gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05374635 |
| Source dataset | uspto-grants-1994_12 |
| ORD ID | ord-83da7649d3774bdc9206a679240a3b34 |
| Source note | uspto-grants-1994_12 |