Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | HCID 90046360 | HCID 90046360 | — |
| Catalyst | HCID 178419072 | HCID 178419072 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 90046309 | HCID 90046309 | — |
Reaction Steps
To a solution of 6-bromo-1-cyclopropyl-5-fluoro-3,3-dimethylindolin-2-one (example 36b, 400 mg, 1.34 mmol) in NMP (7 ml) were added ammonium hydroxide (6.3 g, 7 ml, 44.9 mmol) and copper(I) oxide (38.4 mg, 268 μmol). The reaction mixture was heated in a sealed tube to 110° C. for 24 hours and then poured into dichloromethane (20 ml). The organic phase was washed with 1 M aqueous sodium bicarbonate solution and with water, dried over sodium sulfate and concentrated in vacuo. The NMP was removed by kugelrohr distillation. The residue was purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as off-white crystals (257 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221816B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-ad7defecaf184768879b44b61107c19b |
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| Source note | uspto-grants-2015_12 |
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