6-Methoxyquinoline-2-carbonitrile → HCID 178487953, compound

HRID 1490910

Reaction equation

HRID 1490910 reaction equation
COc1ccc2nc(C#N)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#N)cc(B3OC(C)(C)C(C)(C)O3)c2c1

Participants

6

Reactant 1

HCID 2304816-Methoxyquinoline-2-carbonitrile

Product 1

HCID 178487953HCID 178487953, compoundYield 87%

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
25 °C

Procedure

General procedure B was applied to 6-methoxyquinoline-2-carbonitrile (184 mg, 1.00mmol). The reaction was stirred at room temperature for 48 hours. Upon completion,volatiles were removed under reduced pressure and the remaining residue was purified by silica gel flash-column chromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, affording 6-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline-2-carbonitrile as a off-white solid (270 mg, 87%);

Sources & evidence

ORD record
ord-5c863801736b4499b0d1a54e4561f8db
Source dataset
Borylation dataset from Roche

Linked notes

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