6-Methoxyquinaldine → HCID 178487840, compound

HRID 1490906Notes

Reaction equation

HRID 1490906 reaction equation
COc1ccc2nc(C)ccc2c1>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]>COc1ccc2nc(C)cc(B3OC(C)(C)C(C)(C)O3)c2c1

Participants

6

Reactant 1

HCID 706486-Methoxyquinaldine

Product 1

HCID 178487840HCID 178487840, compoundYield 76%

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-methoxyquinoline (173 mg, 1.00mmol). Purification by silica gel flash-columnchromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, affording 6-methoxy-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)quinolineas an off-white solid (227 mg, 76%);

Sources & evidence

ORD record
ord-eed55d2d7131490b8e23983840915e3e
Source dataset
Borylation dataset from Roche

Reaction notes

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