N,N-Dimethyl 2-pyridinecarboxamide → N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)picolinamide

HRID 1490879Notes

Reaction equation

HRID 1490879 reaction equation
CN(C)C(=O)c1ccccn1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.O=C(Nc1ccccc1-c1ccc(-c2ccccn2)nc1)NC1CCCCC1.[Ir].[Ir]>CN(C)C(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccn1.CN(C)C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cn1

Participants

7

Reactant 1

HCID 12272694N,N-Dimethyl 2-pyridinecarboxamide

Product 2

HCID 49760506N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)picolinamideYield 74%HCID 57416491N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamideYield 12%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 91820779HCID 91820779, compoundReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-753f2e36bb9640f39382d952bbd9b0c6
Source dataset
Borylation dataset from Roche

Reaction notes

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