2-Methyl-7-(trifluoromethyl)quinoline → HCID 178422399, compound

HRID 1490914

Reaction equation

HRID 1490914 reaction equation
Cc1ccc2ccc(C(F)(F)F)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(C(F)(F)F)cc2n1.Cc1ccc2c(B3OC(C)(C)C(C)(C)O3)cc(C(F)(F)F)cc2n1

Participants

7

Reactant 1

HCID 224169042-Methyl-7-(trifluoromethyl)quinoline

Product 2

HCID 178422399HCID 178422399, compoundYield 65%HCID 178422497HCID 178422497, compoundYield 27%

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-(trifluoromethyl)quinoline (211 mg, 1.00mmol). The reaction was stirred at room temperature for 20hours affording 2 monoborylated products in a 70:30 ratio. Volatiles were removed under reduced pressure and the remaining residue was purified by silica gel flash-column chromatography with gradient elution of EtOAc/hexane from 20 -75% over 15 column volumes, to afford with the major isomer (Rf.0.15) 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-(trifluoromethyl)quinoline as a white crystalline solid (219 mg, 65%); m.p.109 -110 °C; Further elution afforded (Rf.0.1) 2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-(trifluoro-methyl)quinoline as an off-white solid (91 mg, 27%); m.p.99 -100 °C;

Sources & evidence

ORD record
ord-9c8606b8f7b74da2b09422cbd3d40722
Source dataset
Borylation dataset from Roche

Linked notes

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