Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 57511328 | HCID 57511328 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66980511 | HCID 66980511 | 77.8% |
Reaction Steps
To a THF (30 mL) suspension of NaH (60% in oil, 1.22 g) was added tert-butyl {4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (7.77 g) at 0° C. After stirring at 0° C. for 10 min, iodomethane (4.33 g) was added and the mixture was stirred at room temperature for 3 hours. The mixture was poured into ice water and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford the title compound (6.30 g) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946437B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-8a0d0d69bf0a480882f3eba6e1148001 |
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| Source note | uspto-grants-2015_02 |
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