Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 67528028 | HCID 67528028 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67528435 | HCID 67528435 | 95% |
Reaction Steps
To a 0° C. solution of {4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-carbamic acid tert-butyl ester (1.9 g, 3.9 mmol) in DMF (15 mL) is added sodium hydride (60% dispersion in mineral oil, 0.19 g, 4.7 mmol) portionwise. The mixture is stirred at 0° C. for 30 minutes. Iodomethane (0.83 g, 5.9 mmol) is added dropwise. The reaction mixture is then stirred at room temperature for 1.0 h. The reaction is quenched with the addition of saturated ammonium chloride (20 mL) at 0° C. The reaction mixture is partitioned between EtOAc (30 mL) and water (20 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound (1.85 g, 95%) as a foamy solid. LC-ES/MS m/e 526.0 (M+23).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07846960B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-3837165dd6f046449f820a0ad2aae789 |
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| Source note | uspto-grants-2010_12 |
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