Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 59497229 | HCID 59497229 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59497544 | HCID 59497544 | 90% |
Reaction Steps
To a solution of 7-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-2,3-dimethyl-1H-indole-6-carboxylic acid methyl ester (107 mg, 0.3 mmol) in THF (10 mL) was added NaH (60% in mineral oil) (22 mg, 0.55 mmol) at 0 C under nitrogen atmosphere. The solution was stirred at the same temperature for 15 minutes. MeI (0.034 mL, 0.55 mmol) was added and the solution was stirred at 0 C for 2 hour. Sat. NH4Cl solution was added and the solution was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 7-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1,2,3-trimethyl-1H-indole-6-carboxylic acid methyl ester (100 mg. 90%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09150556B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-bd5f48d60156407783ce2351eb323ef7 |
|---|
| Source note | uspto-grants-2015_10 |
|---|