6-Bromo-2-methylquinoline → HCID 178422397, compound

HRID 1490908Notes

Reaction equation

HRID 1490908 reaction equation
Cc1ccc2cc(Br)ccc2n1>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]>Cc1cc(B2OC(C)(C)C(C)(C)O2)c2cc(Br)ccc2n1

Participants

6

Reactant 1

HCID 5228856-Bromo-2-methylquinoline

Product 1

HCID 178422397HCID 178422397, compoundYield 84%

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 2-methyl-6-bromoquinoline (222 mg, 1.0 mmol). Purification by silica gel flash-column chromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, affording 6-bromo-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline as a white solid (292 mg, 84%); m.p.124 -125 °C;

Sources & evidence

ORD record
ord-7f6a7ccc899744fc8dc6a748d37e508f
Source dataset
Borylation dataset from Roche

Reaction notes

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