HCID 119085944, compound → HCID 178422403, compound

HRID 1490916Notes

Reaction equation

HRID 1490916 reaction equation
Cc1ccc2ccc([Si](C)(C)C)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([Si](C)(C)C)cc2n1

Participants

6

Reactant 1

HCID 119085944HCID 119085944, compound

Product 1

HCID 178422403HCID 178422403, compoundYield 68%

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-methyl-7-(trimethylsilyl)quinoline (215 mg, 1.00mmol). The reaction was stirred at room temperature for 72hoursaffording a mixture of monoborylated productsin an 85:10:5 ratio 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 only the major 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-(trimethylsilyl)quinoline productas a white solid (231 mg, 68%); m.p.110 -111 °C;

Sources & evidence

ORD record
ord-9cf4b02ff724463e9768d29a6363cf8d
Source dataset
Borylation dataset from Roche

Reaction notes

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