Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 58548420 | HCID 58548420 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67469042 | HCID 67469042 | 34% |
Reaction Steps
To a solution of 2-[1-(3-bromo-pyridin-2-yl)-azetidin-3-yl]-quinoline (150 mg, 0.51 mmol), piperidine (43.35 mg, 0.51 mmol), BINAP (31.1 mg, 0.05 mmol), t-BuONa (196 mg, 2 mmol) in dioxane (15 mL) was added Pd2(dba)3 (45.75 mg, 0.05 mmol) then the reaction mixture was stirred at 90° C. under a N2 atmosphere overnight. The reaction mixture was filtered through CELITE™ and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give [2′-(3-quinolin-2-yl-azetidin-1-yl)-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-yl]-methanol (60 mg, 0.17 mmol, yield 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946230B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-8de995910cfd4347a06a54df38fc3170 |
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| Source note | uspto-grants-2015_02 |
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