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

HRID 1490880Notes

Reaction equation

HRID 1490880 reaction equation
CN(C)C(=O)c1ccccn1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.[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 58%HCID 57416491N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamideYield 30%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-c18f3dd0c2f745d092d4ad27e5b67fd8
Source dataset
Borylation dataset from Roche

Reaction notes

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