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

HRID 1490924Notes

Reaction equation

HRID 1490924 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 66%HCID 178422498HCID 178422498, compoundYield 10%

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

Application of general procedure B with 7-chloro-2-methylquinoline (177 mg. 1.00mmol)for 68 h afforded 73:27 mixture of 13g:14gat 93% conversion, as determined by 1H NMR spectrum analysis of the crude mixture. Purification of the crude mixture, as above, afforded 7-chloro-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline as a white crystalline solid (30mg, 10%)and 7-chloro-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinolineas white crystalline solid (200mg, 66%).

Sources & evidence

ORD record
ord-c01bd39f2b97423a8a4ebcc7c6123050
Source dataset
Borylation dataset from Roche

Reaction notes

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