Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | HCID 66765016 | HCID 66765016 | — |
| Solvent | tetrahydrofuran N,N-dimethylformamide | HCID 21974620 | — |
| Product | HCID 66764944 | HCID 66764944 | — |
Reaction Steps
3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.0752 g, 0.23 mmol) was dissolved in DMF:THF (1:1, 4 mL) and cooled to −78° C. Lithium bis(trimethylsilyl)amide solution (0.500 mL, 0.5 mmol, 1.0M in hexanes) was added. After 1 hour, iodomethane (11 μL, 0.18 mmol) was added and the reaction was allowed to warm to room temperature over 30 minutes then submitted to aqueous workup. Purification by silica gel chromatography (0-100% EtOAc in hexanes) provided the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09000025B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-8573ced97ca04b94b4671b512104fea3 |
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| Source note | uspto-grants-2015_04 |
|---|