2-Methylimidazole → HCID 68708145, compound

HRID 2067932Notes

Reaction equation

HRID 2067932 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[F:7][C:8]([F:19])([F:18])[C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1>C1COCC1>[CH3:1][C:2]1[N:3]([C:12]2[CH:13]=[CH:14][C:9]([C:8]([F:19])([F:18])[F:7])=[CH:10][CH:11]=2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 127492-MethylimidazoleHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 68708145HCID 68708145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methylimidazole (1.0 g, 12 mmol) was dissolved in 35 mL THF. 4-(Trifluoromethyl)phenylboronic acid (2.66 g, 14 mmol) and [Cu(OH)TMEDA]2Cl2 (1.13 g, 2 mmol) were added. Oxygen was bubbled through the reaction mixture for 30 minutes and stirring was continued at room temperature overnight. The reaction mixture was filtered through a dicalite speed plus pad, washed with 80 ml THF and evaporated. The crude product was purified by flash chromatography on silica gel with ethyl acetate. The desired compound was obtained as a light yellow solid (1.6 g, 58%), MS: m/e=227.2 (M+H+).

Workup

  1. customOxygen was bubbled through the reaction mixture for 30 minutes
  2. filtrationThe reaction mixture was filtered through a dicalite speed plus pad
  3. washwashed with 80 ml THF
  4. customevaporated
  5. customThe crude product was purified by flash chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-7c3ab27652cb48009419bb8435ef8ef3
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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