HCID 82573215, compound → HCID 178422401, compound

HRID 1490918Notes

Reaction equation

HRID 1490918 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 86%

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 2-methylquinoline-7-carbonitrile (168 mg, 1.00mmol). The reaction was stirred at room temperature (25 °C) for 48 hours affording a 95:5 mixture of monoborylated products. Volatiles were removed under reduced pressure and the remaining residue was purified by recrystallisation from acetonitrile, affording only 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline-7-carbonitrileas a white solid (252 mg, 86%); m.p.149 -150 °C;

Sources & evidence

ORD record
ord-d83616a1ff6a4fdeae6d42f45005d049
Source dataset
Borylation dataset from Roche

Reaction notes

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