N,N-dihexyl-2-methoxybenzamide → N,N-dihexyl-2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1490834Notes

Reaction equation

HRID 1490834 reaction equation
CCCCCCN(CCCCCC)C(=O)c1ccccc1OC>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]>CCCCCCN(CCCCCC)C(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1OC.CCCCCCN(CCCCCC)C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1OC

Participants

7

Reactant 1

HCID 4321176N,N-dihexyl-2-methoxybenzamide

Product 2

HCID 91820792N,N-dihexyl-2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 13%HCID 140847346N,N-dihexyl-2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 27%

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-e1949cb2eb854ad7bac33c3cd6e6137d
Source dataset
Borylation dataset from Roche

Reaction notes

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