Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1H-Indazole | HCID 9221 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 67211222 | HCID 67211222 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67210409 | HCID 67210409 | 36% |
| Product | HCID 67210582 | HCID 67210582 | 64% |
Reaction Steps
[step 1] Indazole (240 mg, 2.03 mmol) was dissolved in DMF (5.0 mL), sodium hydride (60%, 81 mg, 2.03 mmol) was added, and the mixture was stirred for 15 min. To this mixture was added (E)-2-(8-chloromethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile (300 mg, 1.01 mmol) obtained in Reference Example B5, and the mixture was stirred at room temperature for 3 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to give (E)-2-[8-(indazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (245 mg, 64%) and (E)-2-[8-(indazol-2-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (138 mg, 36%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08486980B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-7a11613c817045778409554aed224dd7 |
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| Source note | uspto-grants-2013_07 |
|---|