N,N-dimethyl-m-toluidine → N,N,3-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

HRID 1490494Notes

Reaction equation

HRID 1490494 reaction equation
Cc1cccc(N(C)C)c1>B1Oc2ccccc2O1.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>Cc1cc(N(C)C)ccc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 8488N,N-dimethyl-m-toluidine

Product 1

HCID 66587807N,N,3-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamineYield 75%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Prepared from N,N,3-trimethylaniline (1e, 13.5 mg, 0.100 mmol, 1.00 equiv) and catBH (18.0 mg, 0.150 mmol, 1.50 equiv) according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3e (19.6 mg, 75%) as a white solid.

Sources & evidence

ORD record
ord-c7114d160d51495cb17e79010eb2e33b
Source dataset
Borylation dataset from Roche

Reaction notes

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