Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 5-Fluoroindole | HCID 67861 | — |
| Reactant | HCID 309016 | HCID 309016 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18385285 | HCID 18385285 | 110.5% |
Reaction Steps
Sodium hydride (55% dispersion in oil, 63 mg, 1.44 mmol) was added to a solution of 5-fluoro-indol (150 mg, 1.11 mmol) in dry DMF (3 mL). The mixture was stirred under nitrogen for 15 min. 2-(3-Bromomethyl-benzyl)-isoindole-1,3-dione (403 mg, 1.22 mmol) was added and the mixture was stirred at room temperature over night. After cooling, aqueous methylamine (40%, 5 mL) was added and this mixture was heated at 80° C. over night. Ethyl acetate was added and the organic phase was washed three times with water, brine, dried and concentrated to give 312 mg of the sub-title compound sufficiently pure for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06492406B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-6e38a33fefc04f6d9494f806127a45e4 |
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| Source note | uspto-grants-2002_12 |
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