7-Bromo-2-methylquinoline → HCID 178422398, compound

HRID 1490911Notes

Reaction equation

HRID 1490911 reaction equation
Cc1ccc2ccc(Br)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(Br)cc2n1.Cc1ccc2c(B3OC(C)(C)C(C)(C)O3)cc(Br)cc2n1

Participants

7

Reactant 1

HCID 123328967-Bromo-2-methylquinoline

Product 2

HCID 178422398HCID 178422398, compoundYield 52%HCID 178422496HCID 178422496, compoundYield 28%

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 with 7-bromo-2-methylquinoline (221 mg, 1.00mmol) afforded a mixture of 2 monoborylated products in a 65:35ratio, as determined by GC-MS.

Sources & evidence

ORD record
ord-c929c013efd04889bc74482e72cb999d
Source dataset
Borylation dataset from Roche

Reaction notes

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