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5-Bromoindole → 5-Bromo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

HRID 1490420
Notes
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Reaction equation

HRID 1490420 reaction equation
Brc1ccc2[nH]ccc2c1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.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(c2cc(Br)cc3cc[nH]c23)OC1(C)C
ParticipantsConditionsSources & evidenceReaction notes

Participants

7

Reactant 1

HCID 249055-Bromoindole

Product 1

HCID 1015026765-Bromo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleYield 55%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 82923Chloro-1,5-cyclooctadiene-iridium(I) dimerCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-13c0c1541ad04aae82c7de52486d80e6
Source dataset
Borylation dataset from Roche
DOI
10.1021/ja1006405

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes