HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490923Generated: October 30, 2026
7-Chloro-2-methylquinoline → HCID 178422400, compound
https://huagongshe.com/reaction/1490923
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 7-Chloro-2-methylquinoline | HCID 138395 | — |
| 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 178422400 | HCID 178422400 | 61% |
| Product | HCID 178422498 | HCID 178422498 | 11% |
Reaction Steps
General procedure A was applied to 7-chloro-2-methylquinoline (177 mg. 1.00mmol). The reaction afforded a 65:35 mixture of 2 monoborylated productsat 92% conversion,as determined by GC-MS. Purification by silica gel flash-column chromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, afforded a mixture of 7-chloro-2-methylquinoline and 7-chloro-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinolineas yellow oil. Recrystallisation from minimum amount of MeCN afforded 7-chloro-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline as a white crystalline solid (33mg, 11%); m.p.149 -150 °C; Further elution afforded 7-chloro-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinolineas white crystalline solid (185 mg, 61 %)
Provenance & Evidence
| DOI | 10.1039/c2sc20776a |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-e25987c0baf547b890f7899b0c1390b5 |
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| Source note | Borylation dataset from Roche |
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