HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,6-Dibromopyridine → 4-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,6-Dibromopyridine | HCID 12274 | — |
| Reactant | 4-(Benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline | HCID 58387605 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline | HCID 58387598 | 36% |
Reaction Steps
A solution of 4-(benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1.0 equiv.), 2,6 dibromopyridine (1.0 equiv.) and Pd(dppf)Cl2—CH2Cl2 (0.1 equiv.) in 3:1 DME/2M Na2CO3 was heated in a microwave at 100° C. for 20 minutes. Upon cooling, the solution was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (70-90 EtOAc/hexanes eluant) to yield 4-(benzyloxy)-6-(6-bromopyridin-2-yl)quinoline (36%). LC/MS=391.1/393.1 (M+H), LC=3.36 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735424B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-d06e05df8eb54070b3bb3b6979c81e73 |
| Source note | uspto-grants-2014_05 |