Water → N'-(4'-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide

HRID 1673190Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([N:22]=[CH:23][N:24]([CH2:26][CH3:27])[CH3:25])=[C:17]([CH3:28])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC.C1CCCCC1.CC(C)=O.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH3:28])[C:18]([N:22]=[CH:23][N:24]([CH2:26][CH3:27])[CH3:25])=[CH:19][C:20]=2[CH3:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 0.3 g (1.8 mmol) of (4-tert-butylphenyl)boronic acid, 0.4 g (1.5 mmol) of N′-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, 1.5 g (4.5 mmol) caesium carbonate and 0.03 g (0.03 mmol) tetrakis(triphenylphosphin)palladium in 3.5 ml of 1,2-dimethoxyethan was stirred for 16 hrs at 80° C. At room temperature 5 ml of water and 15 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 15 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographic (cyclohexane/aceton:4/1) yielded 0.23 g (0.7 mmol) 47% of N′-(4′-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.67.

Workup

customThe organic layer was separated
extractionthe watery layer was again extracted
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e3b4173cda6346a496064ade31435d05
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999137B2

Reaction notes

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