HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490914Generated: October 26, 2026
2-Methyl-7-(trifluoromethyl)quinoline → HCID 178422399, compound
https://huagongshe.com/reaction/1490914
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Methyl-7-(trifluoromethyl)quinoline | HCID 22416904 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | 4,4'-Di-tert-butyl-2,2'-bipyridyl | HCID 4249187 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | HCID 178422399 | HCID 178422399 | 65% |
| Product | HCID 178422497 | HCID 178422497 | 27% |
Reaction Steps
General procedure B was applied to 2-methyl-7-(trifluoromethyl)quinoline (211 mg, 1.00mmol). The reaction was stirred at room temperature for 20hours affording 2 monoborylated products in a 70:30 ratio. Volatiles were removed under reduced pressure and the remaining residue was purified by silica gel flash-column chromatography with gradient elution of EtOAc/hexane from 20 -75% over 15 column volumes, to afford with the major isomer (Rf.0.15) 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-(trifluoromethyl)quinoline as a white crystalline solid (219 mg, 65%); m.p.109 -110 °C; Further elution afforded (Rf.0.1) 2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-(trifluoro-methyl)quinoline as an off-white solid (91 mg, 27%); m.p.99 -100 °C;
Provenance & Evidence
| DOI | 10.1039/c2sc20776a |
|---|
| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-9c8606b8f7b74da2b09422cbd3d40722 |
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| Source note | Borylation dataset from Roche |
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