Methyldiphenylamine → N-Methyl-N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

HRID 1490492Notes

Reaction equation

HRID 1490492 reaction equation
CN(c1ccccc1)c1ccccc1>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>CN(c1ccccc1)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1

Participants

7

Reactant 1

HCID 11098Methyldiphenylamine

Product 1

HCID 165993412N-Methyl-N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamineYield 35%

Reagents, catalysts & solvents 5

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

Conditions

Temperature
120 °C

Procedure

Prepared from N-methyl-N-phenylaniline (1c, 55.0 mg, 0.300 mmol, 1.00 equiv) and catBH (54.0 mg, 0.450 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 3c (32.5 mg, 35%) as a white solid.

Sources & evidence

ORD record
ord-494fdd9d223f4b0b87a2959a1dd9d85b
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…