Quinoline, 2,7-dimethyl- → HCID 146014097, compound

HRID 1490922Notes

Reaction equation

HRID 1490922 reaction equation
Cc1ccc2ccc(C)nc2c1>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]>Cc1ccc2c(B3OC(C)(C)C(C)(C)O3)cc(C)nc2c1

Participants

6

Reactant 1

HCID 7138Quinoline, 2,7-dimethyl-

Product 1

HCID 146014097HCID 146014097, compoundYield 80%

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 2,7-dimethylquinoline (157 mg, 1.00mmol). The reaction was stirred at room temperature (25 °C) for 72 hours. Analysis by GC-MS showed a 95:5 mixture of 2 monoborylated products. Volatiles were removed from the reaction 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 the major isomer, 2,7-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline, as an off-white solid (226 mg, 80%); m.p.108 -109 °C

Sources & evidence

ORD record
ord-48ecdbcd37ca46938b19f539f4fc4ebe
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…