Isoquinoline, 1-(1-naphthalenyl)- → HCID 101547934, compound

HRID 1491477Notes

Reaction equation

HRID 1491477 reaction equation
c1ccc2c(-c3nccc4ccccc34)cccc2c1>C(C=NN(Cc1ccccc1)Cc1ccccc1)=NN(Cc1ccccc1)Cc1ccccc1.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.[Cl-].[Cl-].[Ir].[Ir]>CC1(C)OB(c2ccc3ccccc3c2-c2nccc3ccccc23)OC1(C)C

Participants

7

Reactant 1

HCID 3838254Isoquinoline, 1-(1-naphthalenyl)-

Product 1

HCID 101547934HCID 101547934, compoundYield 75%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 89456011N-benzyl-N-[2-(dibenzylhydrazinylidene)ethylideneamino]-1-phenylmethanamineReagentHCID 82923Chloro-1,5-cyclooctadiene-iridium(I) dimerCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Following the general procedure, column chromatography (EtOAc/nhexane 1:3) afforded 9a (160 mg, 84 %) as a light yellow solid. Evaporation from EtOAc/n-hexane afforded X-Ray quality crystals.

Sources & evidence

ORD record
ord-cbd29274a8a74bd9b7a24ac995b10d59
Source dataset
Borylation dataset from Roche

Reaction notes

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