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

HRID 1466421Notes

Reaction equation

HRID 1466421 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, 03 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), 734 (m, 3H), 7.47 (ol, 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-52d20106d481436f912bcbd98664d034
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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