1,5-Dimethylpyrrole-2-carbonitrile → 1,5-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carbonitrile

HRID 1491468Notes

Reaction equation

HRID 1491468 reaction equation
Cc1ccc(C#N)n1C>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>Cc1c(B2OC(C)(C)C(C)(C)O2)cc(C#N)n1C.Cc1cc(B2OC(C)(C)C(C)(C)O2)c(C#N)n1C

Participants

7

Reactant 1

HCID 918121,5-Dimethylpyrrole-2-carbonitrile

Product 2

HCID 532171601,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carbonitrileYield 14%HCID 532171711,5-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carbonitrileYield 66%

Reagents, catalysts & solvents 4

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-86987cba45f54bfdab60c6e33a96a8bd
Source dataset
Borylation dataset from Roche

Reaction notes

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