HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Bromopyridine → 3-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Bromopyridine | HCID 12286 | — |
| Reactant | 3,7-Diazabicyclo(3.3.1)nonane | HCID 192720 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 3-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane | HCID 9920686 | 25% |
Reaction Steps
3,7-Diazabicyclo[3.3.1]nonane, prepared as described in (Garrison, G. L. et. al., J. Org. Chem. 58, 27, (1993) 7670), and 3-bromopyridine were processed as described in Example 1A. The proportions of reagents were changed from Example 1A to the following: Pd2(dba)3 (0.02 eq), BINAP (0.05 eq), and NaOt-Bu (1.7 eq). The title compound was obtained in 25% yield after purification by flash chromatography (silica gel; CHCl3:MeOH:NH4OH; 90:5:1). MS (DCI/NH3) m/z 204 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07265115B2 |
| Source dataset | uspto-grants-2007_09 |
| ORD ID | ord-6811a3758a684bb1a9697c9923b6bd4d |
| Source note | uspto-grants-2007_09 |