N,N,N',N'-Tetramethylethylenediamine → 1-(4-Bromophenyl)-2-(2-chlorophenyl)-4-(trifluoromethyl)-1H-imidazole

HRID 1046642Notes

Reaction equation

HRID 1046642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.CN(CCN(C)C)C>ClCCl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N:9]2[CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[N:12]=[C:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 79599(4-Bromophenyl)boronic acidHCID 178506247HCID 178506247, compound

Product 1

HCID 592513781-(4-Bromophenyl)-2-(2-chlorophenyl)-4-(trifluoromethyl)-1H-imidazoleYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(2-Chloro-phenyl)-4-trifluoromethyl-1H-imidazole (370 mg, 1.5 mmol), 4-bromo-phenylboronic acid (600 mg, 3 mmol), and [Cu(OH).TMEDA]2Cl2 (140 mg, 0.3 mmol) were mixed with 6 mL dry dichloromethane, and stirred at room temperature under atmosphere of dioxygen for 2 days. The reaction mixture was diluted with dichloromethane and filtered through celite. The filtrate was concentrated under vacuum, and the residue was purified by chromatography on silica gel (Hexane/EtOAc 8/2) to give a solid (151 mg, 25% yield). 1H-NMR (400 MHz, CDCl3): δ 7.02 (d, 2H), 7.34 (m, 3H), 7.47 (d, 2H), 7.53 (dd, 1H), 7.56 (dd, 1H).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was purified by chromatography on silica gel (Hexane/EtOAc 8/2)

Sources & evidence

ORD record
ord-b9b40158ad2d4e88acaf9d70e77adac5
Source dataset
uspto-grants-2013_10
Patent number
US08569352B2

Reaction notes

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