N-Methyl-p-toluamide → N,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1491053Notes

Reaction equation

HRID 1491053 reaction equation
CNC(=O)c1ccc(C)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1[nH]c2c(NC(=O)c3ccc(-c4ccccn4)nc3)cccc2c1C.[Ir].[Ir]>CNC(=O)c1ccc(C)cc1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 140377N-Methyl-p-toluamide

Product 1

HCID 169546367N,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 61%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 178433626HCID 178433626, compoundReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 2:1) as the eluent.

Sources & evidence

ORD record
ord-89c0c19890bc4624973e1e0c5b5c3b97
Source dataset
Borylation dataset from Roche

Reaction notes

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