Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | 2-Bromopyrimidine | HCID 78345 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline | HCID 86682426 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86682424 | HCID 86682424 | 87% |
Reaction Steps
To 1.21 g (1.79 mmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 10, 0.90 g (5.7 mmol) of 2-bromopyrimidine, 1.0 ml (5.9 mmol) of diisopropylethylamine and 20 ml of tert-butanol were added, and the reaction solution was stirred at 65° C. for 2.5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. n-Hexane was added to the obtained residue and the precipitate was obtained by filtration to provide 1.17 g of the title compound as a white solid (yield: 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187450B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-2ae7482843c44512a98db353f2aed498 |
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| Source note | uspto-grants-2015_11 |
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