1-(2-Methoxyphenyl)isoquinoline → 1-[2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]isoquinoline

HRID 1491494

Reaction equation

HRID 1491494 reaction equation
COc1ccccc1-c1nccc2ccccc12>C(=NN(Cc1ccccc1)Cc1ccccc1)c1ccccn1.C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>COc1cccc(B2OC(C)(C)C(C)(C)O2)c1-c1nccc2ccccc12

Participants

7

Reactant 1

HCID 231597341-(2-Methoxyphenyl)isoquinoline

Product 1

HCID 1015479381-[2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]isoquinolineYield 88%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 67601456N,N-Dibenzyl-N'-(pyridin-2-ylmethylene)hydrazineReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Following the general procedure, precipitation from the reaction crude with hexane and trituration afforded 9i (159 mg, 88 %) as a pale solid.

Sources & evidence

ORD record
ord-2dd73b1c305947e1a593c90545f7d2d2
Source dataset
Borylation dataset from Roche

Linked notes

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