Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | HCID 86628518 | HCID 86628518 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66839133 | HCID 66839133 | 51.9% |
Reaction Steps
Triethylsilane (40.9 μL) and a 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride-dichloromethane complex (4.37 mg) were added to a solution of 3-(4-methyl-1H-imidazol-1-yl)-6-{(E)-2-[8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]vinyl}pyridin-2-yl trifluoromethanesulfonate (64 mg) in DMF (2 mL). The reaction solution was stirred at 70° C. for five hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=4:1→ethyl acetate) to obtain a racemate of the title compound (25 mg). The resulting racemate (25 mg) was separated by CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm, mobile phase: ethanol, flow rate: 11 mL/min) to obtain the title optically active compound with a retention time of 21 minutes and positive optical rotation (10 mg) and the title optically active compound with a retention time of 30 minutes and negative optical rotation (10 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07935815B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-d4a66a1c715c43aca60d6a0399954702 |
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| Source note | uspto-grants-2011_05 |
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