HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfide → HCID 67109216, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfide | HCID 1068 | — |
| Reactant | Boron trifluoride | HCID 6356 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67109665 | HCID 67109665 | — |
| Catalyst | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 67109216 | HCID 67109216 | 58.3% |
Reaction Steps
5-chloro-2-(2,4-dimethylthiophen-3-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile (75 mg, 0.19 mmol) was dissolved in 4 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.20 ml, 1.91 mmol) was added drop wise and the mixture was stirred at room temperature for 24 h. A few drops MeOH were added at 0° C. followed by NaHCO3 (aq, sat) and brine. The layers were separated and the organic layer was concentrated. The crude product was purified on silica (MeOH/DCM 1:99). 42.0 mg 5-chloro-2-(2,4-dimethylthiophen-3-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08710243B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-7c37dd2d159845a68140a97ab38887d6 |
| Source note | uspto-grants-2014_04 |