N,N-dimethyl-m-toluidine → HCID 102111590, compound

HRID 1490548Notes

Reaction equation

HRID 1490548 reaction equation
Cc1cccc(N(C)C)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>Cc1cc(B2OC(C)(C)C(C)(C)O2)cc(N(C)C)c1

Participants

6

Reactant 1

HCID 8488N,N-dimethyl-m-toluidine

Product 1

HCID 102111590HCID 102111590, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using N,N,3-trimethylaniline (73.5 ul, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 24 hours at 100 oC. 5d was obtained as white solid (126.2 mg, 96%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v). m.p.: 82-84 °C.

Sources & evidence

ORD record
ord-710cd7e708874f91a311c72c189c779a
Source dataset
Borylation dataset from Roche

Reaction notes

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