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4-Chloro-2-methyl-7-azaindole → 4-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1490441
Notes
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Reaction equation

HRID 1490441 reaction equation
Cc1cc2c(Cl)ccnc2[nH]1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1cnc2c(ccc3c(C)c(C)cnc32)c1C.[Ir].[Ir]>Cc1cc2c(Cl)c(B3OC(C)(C)C(C)(C)O3)cnc2[nH]1
ParticipantsConditionsSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 210816754-Chloro-2-methyl-7-azaindole

Product 1

HCID 1018796714-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridineYield 64%

Reagents, catalysts & solvents 4

HCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-a20bcd5fbd4546689750c87276985fa6
Source dataset
Borylation dataset from Roche
DOI
10.1021/ja412563e

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes