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

Reaction equation

CNC(=O)c1cccc(C)c1>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)c1cc(C)ccc1B1OC(C)(C)C(C)(C)O1

Participants

Conditions

Temperature: 60 °C

Procedure

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

Sources & evidence

ORD record: ord-b15e03684040477e867fb0e7118ab17a
Source dataset: Borylation dataset from Roche
DOI: 10.1002/anie.201907366

Reaction notes

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Participants

Reactant 1

HCID 966002N,3-dimethylbenzamide

Product 1

HCID 133668341N,5-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 45%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagent

HCID 178433626HCID 178433626, compoundReagent

HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalyst

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature: 60 °C

Procedure

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

Sources & evidence

ORD record: ord-b15e03684040477e867fb0e7118ab17a
Source dataset: Borylation dataset from Roche
DOI: 10.1002/anie.201907366

Reaction notes

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