HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (R)-3-[2-Oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (R)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester | HCID 58497430 | — |
| Reactant | trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide | HCID 131730211 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (R)-3-[2-Oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester | HCID 58497410 | 81% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
To a solution of (R)-3-(2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (refer to example 2) (80 mg, 0.26 mmol) in DMF (10 mL) were added trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide (138 mg, 0.39 mmol) and K2CO3 (71 mg, 0.51 mmol) at room temperature. The solution was heated at 100° C. for 4 hours. The solution was cooled and was extracted with water and EtOAc. The combined organic layer was dried with MgSO4 and filtered. The filtrate was concentrated and the residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent to afford the title compound (100 mg, 81%) as white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09062056B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-3112dc9392224cd2b212d672e67debcc |
| Source note | uspto-grants-2015_06 |