Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 178494047 | HCID 178494047 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 178514695 | HCID 178514695 | 77.2% |
Reaction Steps
To a solution of 4-(1-(trans-4-((tert-butyl(dimethyl)silyl)oxy)cyclohexyl)-4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)benzenesulfonamide (10.0 mg) in acetonitrile (1 mL) were added sodium iodide (7.3 mg) and chloro(trimethyl)silane (0.025 mL), and the mixture was stirred overnight at 50° C. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol) to give the title compound (5.8 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09371320B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-89049d2ef2dd4c7e9f0862e988e3a556 |
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| Source note | uspto-grants-2016_06 |
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