Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Sulfide | HCID 1068 | — |
| Reactant | Boron trifluoride | HCID 6356 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67109272 | HCID 67109272 | — |
| Catalyst | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67108811 | HCID 67108811 | 47.4% |
Reaction Steps
2-(3,5-dimethylisothiazol-4-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile (38 mg, 0.11 mmol) was dissolved in 10 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.56 ml, 5.29 mmol) was added drop wise and the mixture was stirred at 0-2° C. for 16 h. A few drops MeOH were added followed by NaHCO3 (aq, sat). The layers were separated and the organic layer was concentrated. The crude product was purified by preparative HPLC. 18.0 mg 2-(3,5-dimethylisothiazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08710243B2 |
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| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-234f5d35a471443b86e7568f1127c9d9 |
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| Source note | uspto-grants-2014_04 |
|---|
