Dichloromethane → 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(pyridin-2-yl)phenyl)aniline

HRID 539470Notes

Reaction equation

HRID 539470 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:13]3[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=3[CH:22]([CH3:24])[CH3:23])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].[C:31]1([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)[CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.ClCCl>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:22]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[C:13]=1[N:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[N:37]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=2)[CH:39]=1)([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 23676156Sodium t-butoxideHCID 68023588N-phenyl-3-(pyridin-2-yl)anilineHCID 706542932-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole

Product 1

HCID 706542913-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(pyridin-2-yl)phenyl)anilineYield 91.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 7237O-XyleneSolvent

Procedure

2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (2.8 g, 7.30 mmol), Pd2(dba)3 (0.067 g, 0.073 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (0.120 g, 0.292 mmol), and sodium t-butoxide (1.053 g, 10.96 mmol) were mixed in 100 mL of xylene. The solution was bubbled with nitrogen for 20 min. N-phenyl-3-(pyridin-2-yl)aniline (1.979 g, 8.03 mmol) was added. The reaction was heated up to reflux for 6 h. After cooled to rt, dichloromethane was added. The mixture was filtered through Celite®. The solvent was then evaporated. The residue was coated on Celite® and columned with hexanes/ethyl acetate (3:1) to give 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(pyridin-2-yl)phenyl)aniline (3.66 g, 6.67 mmol, 91% yield).

Workup

  1. customThe solution was bubbled with nitrogen for 20 min
  2. temperatureThe reaction was heated up
  3. temperatureto reflux for 6 h
  4. filtrationThe mixture was filtered through Celite®
  5. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-887f6bfea39f423cbfb3329e07ac4a04
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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