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

HRID 1490913

Reaction equation

HRID 1490913 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 57%HCID 178422497HCID 178422497, compoundYield 38%

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
100 °C

Procedure

Application of general procedure A to 2-methyl-7-(trifluoromethyl)quinoline (211 mg, 1.00mmol) afforded 2 monoborylated products as a 60:40 ratio.

Sources & evidence

ORD record
ord-297c3aeb46f14a219f8a39f08fe03a57
Source dataset
Borylation dataset from Roche

Linked notes

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