4,7-Dichloroquinoline → HCID 178431097, compound

HRID 1490904Notes

Reaction equation

HRID 1490904 reaction equation
Clc1ccc2c(Cl)ccnc2c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2cnc3cc(Cl)ccc3c2Cl)OC1(C)C

Participants

6

Reactant 1

HCID 68664,7-Dichloroquinoline

Product 1

HCID 178431097HCID 178431097, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

General procedure A was applied to 4-chloro-7-(trifluoromethyl)quinoline (231 mg, 1.00mmol). Purification by recrystallisation from acetonitrile, afforded 4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-7-(trifluormethyl)quinoline as a white solid (289 mg, 81%); m.p.93 -94 °C;

Sources & evidence

ORD record
ord-8075208314464b8da8768d3f69e247d9
Source dataset
Borylation dataset from Roche

Reaction notes

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