Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Bromoethyl methyl ether | HCID 80972 | — |
| Reactant | HCID 118534015 | HCID 118534015 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 117798739 | HCID 117798739 | 82% |
Reaction Steps
To a solution of 4-[(4-chlorobenzyl)oxy]-1-[2-(2-hydroxyethyl)-3-methyl-2H-indazol-5-yl]pyridin-2(1H)-one (30 mg) in N,N-dimethylformamide (2 ml) was added 60% sodium hydride (3.51 mg) at 0° C., and the mixture was stirred at room temperature for 30 min. To the obtained reaction mixture was added (2-bromoethyl)methyl ether (15.3 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (28.1 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199963B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-d3696cb22902479bb09e66be5aaf8c72 |
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| Source note | uspto-grants-2015_12 |
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