Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 5-Methoxyindole | HCID 13872 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 43152078 | HCID 43152078 | — |
Reaction Steps
To a solution of 5-methoxy-1H-indole (500 mg, 3.40 mmol) in dry DMF (8 ml), cooled at 0° C., sodium hydride (60% w/w dispersion in mineral oil, 136 mg, 3.40 mmol) was slowly added portionwise and the reaction was stirred at 0° C. for 45 minutes; then methyl 2-bromoacetate (315 μl, 3.40 mmol) was added dropwise, and the reaction was stirred at room temperature for 15 hours. Water was slowly added, and the product was extracted with Et2O and then with ethyl acetate. The combined organic layers were washed with water, dried over Na2SO4 and evaporated to dryness. The title compound was obtained and used for the next step without further purification (745 mg, 3.40 mmol, quantitative yield). MS/ESI+ 220.1 [MH]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09024027B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-25b2922d4fa8455e9b1dffbdbf33088f |
|---|
| Source note | uspto-grants-2015_05 |
|---|