Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,5,6,7-Tetrahydro-1H-cyclopenta[c]pyridin-1-one | HCID 14732815 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 14732816 | HCID 14732816 | 67% |
Reaction Steps
The title compound of step 5 (260 mg, 1.93 mmol) was dissolved in DMF (5 mL) and cooled to 0° C. NaH (94 mg, 2.31 mmol) was added and the mixture was stirred for 30 min. Methyl iodide (146 μL, 2.31 mmol) was added and the mixture stirred at rt for 2 h. The volatile components were removed under vacuum and silica gel chromatography (PE/EtOAc=1:1) gave the title compound (192.6 mg, 67%) as a brown oil. 1H NMR (CD3Cl, 300 MHz): δ 7.13 (d, J=6.6 Hz, 1H), 6.13 (d, J=6.6 Hz, 1H), 3.53 (s, 3H), 2.79-2.85 (m, 4H), 2.01-2.11 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09034900B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-e7f450bfba26452db03edc93f70abdf0 |
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| Source note | uspto-grants-2015_05 |
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