Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 59497633 | HCID 59497633 | — |
| Reactant | HCID 67361249 | HCID 67361249 | — |
| Product | HCID 59497321 | HCID 59497321 | 76% |
Reaction Steps
To a solution of 100 mg (0.37 mmol) of 2-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-cyclopent-1-enecarboxylic acid ethyl ester in 5 mL of DMF was added 101 mg (0.73 mmol, 2.0 eq.) of potassium carbonate followed by 190 mg (0.55 mmol, 1.5 eq.) indole ammonium iodide at room temperature under nitrogen atmosphere. The resulting suspension was heated to 100° C. for 4 hours. The solution was cooled and stirred at RT over night. The reaction was poured into water and extracted with EtOAc (3×). The combined organics were washed with water, brine and dried (magnesium sulfate). Filtration and concentration gave the crude product which was absorbed onto silica gel and purified via CombiFlash to give 120 mg (76%) of the desired product as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09150556B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-3d9aa6eee4a5407fbfc2b83740cbd2a1 |
|---|
| Source note | uspto-grants-2015_10 |
|---|