4-Fluorophenylboronic acid → 2-Cyclopropyl-1-(4-fluoro-phenyl)-4-iodo-1H-imidazole

HRID 860149Notes

Reaction equation

HRID 860149 reaction equation
[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([I:9])[N:8]=2)[CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1>C1COCC1>[CH:1]1([C:4]2[N:5]([C:14]3[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=3)[CH:6]=[C:7]([I:9])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 178506557HCID 178506557, compound

Product 1

HCID 691201812-Cyclopropyl-1-(4-fluoro-phenyl)-4-iodo-1H-imidazoleYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Cyclopropyl-4-iodo-1H-imidazole (500 mg, 2.14 mmol) was dissolved in 20 ml THF. 4-Fluorobenzene boronic acid (613 mg, 4.38 mmol) and [Cu(OH)TMEDA]2Cl2 (347 mg, 0.75 mmol) were added. Oxygen was bubbled through the reaction mixture for 60 min and stirring was continued under an oxygen atmosphere at RT overnight. The reaction mixture was filtered through a dicalite speed plus pad and washed with 30 mL ethyl acetate. After drying the crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10→50:50 gradient) to get the desired compound as a white solid (320 mg, 46%), MS: m/e=329.1 (M+H+). Preparation of the Compounds of Formula I

Workup

  1. customOxygen was bubbled through the reaction mixture for 60 min
  2. filtrationThe reaction mixture was filtered through a dicalite speed plus pad
  3. washwashed with 30 mL ethyl acetate
  4. dry with materialAfter drying the crude product
  5. customwas purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10→50:50 gradient)

Sources & evidence

ORD record
ord-70d3893b3eaf4568b84b4a27b940c5c9
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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