Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Methyloxybenzyl chloride | HCID 69993 | — |
| Reactant | 4-Bromo-3-methyl-1H-indole | HCID 52987704 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86700759 | HCID 86700759 | 99% |
Reaction Steps
4-Bromo-3-methyl-1H-indole (1.33 g) was dissolved in dimethylformamide (20 mL), and sodium hydride (0.33 g) was added thereto under ice-cooling. After stirring at 0° C. for 15 minutes, p-methoxybenzyl chloride (0.95 mL) was added thereto. The reaction solution was stirred under heating at 70° C. for 30 minutes and partitioned between ethyl acetate and 1M HCl aqueous solution. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (45a) (2.09 g, 99%) as a colorless oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09120780B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-62e5f13f368147e08a291525d54f4e8a |
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| Source note | uspto-grants-2015_09 |
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