5-Bromopyridine-2-carbonitrile → 5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile

HRID 1491469Notes

Reaction equation

HRID 1491469 reaction equation
N#Cc1ccc(Br)cn1>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]>CC1(C)OB(c2cc(Br)cnc2C#N)OC1(C)C.CC1(C)OB(c2cc(C#N)ncc2Br)OC1(C)C

Participants

7

Reactant 1

HCID 8171545-Bromopyridine-2-carbonitrile

Product 2

HCID 497604765-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrileYield 29%HCID 713036785-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrileYield 52%

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-df50bffb88a24ca692339016f6e8a2c2
Source dataset
Borylation dataset from Roche

Reaction notes

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