7-Chloro-2-methylquinoline → HCID 178422400, compound

HRID 1490923Notes

Reaction equation

HRID 1490923 reaction equation
Cc1ccc2ccc(Cl)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(Cl)cc2n1.Cc1ccc2c(B3OC(C)(C)C(C)(C)O3)cc(Cl)cc2n1

Participants

7

Reactant 1

HCID 1383957-Chloro-2-methylquinoline

Product 2

HCID 178422400HCID 178422400, compoundYield 61%HCID 178422498HCID 178422498, compoundYield 11%

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

General procedure A was applied to 7-chloro-2-methylquinoline (177 mg. 1.00mmol). The reaction afforded a 65:35 mixture of 2 monoborylated productsat 92% conversion,as determined by GC-MS. Purification by silica gel flash-column chromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, afforded a mixture of 7-chloro-2-methylquinoline and 7-chloro-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinolineas yellow oil. Recrystallisation from minimum amount of MeCN afforded 7-chloro-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline as a white crystalline solid (33mg, 11%); m.p.149 -150 °C; Further elution afforded 7-chloro-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinolineas white crystalline solid (185 mg, 61 %)

Sources & evidence

ORD record
ord-e25987c0baf547b890f7899b0c1390b5
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…