7-Methoxy-2-methylquinoline → HCID 178486990, compound

HRID 1490920Notes

Reaction equation

HRID 1490920 reaction equation
COc1ccc2ccc(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]>COc1ccc2c(B3OC(C)(C)C(C)(C)O3)cc(C)nc2c1

Participants

6

Reactant 1

HCID 107023617-Methoxy-2-methylquinoline

Product 1

HCID 178486990HCID 178486990, compoundYield 73%

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-methoxy-2-methylquinoline (173 mg, 1.00mmol). The reaction was stirred at room temperature for 48 hours affording a 95:5 mixture of 2 monoborylated products as determined by GC-MS. Volatiles were removed 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 7-methoxy-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)quinolineproduct as a pale yellow solid (218 mg, 73%); m.p.87 -88 °C;

Sources & evidence

ORD record
ord-e480dfec5b664f3bbe97017be0f19814
Source dataset
Borylation dataset from Roche

Reaction notes

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