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

HRID 1490912Notes

Reaction equation

HRID 1490912 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 65%HCID 178422496HCID 178422496, compoundYield 15%

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 7-bromo-2-methylquinoline (222mg, 1.00mmol). The reaction was stirred at room temperaturefor 48 hoursto afford a mixture of 2 monoborylated isomers in a 80:20ratio. Purification by silica gel flash-column chromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, afforded the major product, (Rf0.1) 7-bromo-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline, as a white solid (225 mg, 65%); m.p.149 -150 °C; Further elution afforded (Rf0.05) 7-bromo-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline a white solid (52 mg, 15%); m.p.151 -152 °C;

Sources & evidence

ORD record
ord-56559ffb4c0d47d6b9534101d8e9390e
Source dataset
Borylation dataset from Roche

Reaction notes

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