HCID 82573215, compound → HCID 178422401, compound

HRID 1490917Notes

Reaction equation

HRID 1490917 reaction equation
Cc1ccc2ccc(C#N)cc2n1>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)c2ccc(C#N)cc2n1

Participants

6

Reactant 1

HCID 82573215HCID 82573215, compound

Product 1

HCID 178422401HCID 178422401, compoundYield 78%

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

Application of general procedure A(but with a reaction time of 0.25 hours)with 2-methylquinoline-7-carbonitrile (168 mg, 1.00mmol) afforded a mixture of 2 monoborylated and 1 bisborylated product in an 82:9:9ratio, as determined by GC-MS.

Sources & evidence

ORD record
ord-866a6d3063904e86bbbfa0f6dbabb9f0
Source dataset
Borylation dataset from Roche

Reaction notes

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