Ethyl 2-pyridinecarboxylate → Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate

HRID 1490882Notes

Reaction equation

HRID 1490882 reaction equation
CCOC(=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]>CCOC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccn1.CCOC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cn1

Participants

7

Reactant 1

HCID 17307Ethyl 2-pyridinecarboxylate

Product 2

HCID 9970710Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinateYield 40%HCID 11778242Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylateYield 52%

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-9766272943364fd583084c619b1b8e66
Source dataset
Borylation dataset from Roche

Reaction notes

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