Triethylamine → HCID 69120483, compound

HRID 860153Notes

Reaction equation

HRID 860153 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH3:7])[NH:5][CH:6]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.CCN(CC)CC>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:5]2[CH:6]=[C:2]([I:1])[N:3]=[C:4]2[CH3:7])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 178433060HCID 178433060, compound

Product 1

HCID 69120483HCID 69120483, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Iodo-2-methyl-1H-imidazole (200 mg, 1.0 mmol), 4-fluorophenylboronic acid (215 mg, 1.6 mmol), copper(II)acetate (210 mg, 1.2 mmol) and Et3N (0.16 ml, 1.2 mmol) were suspended in 10 ml THF and oxygen was bubbled through the reaction mixture for 40 min. The reaction mixture was stirred for 48 hours at RT and then filtrated over dicalit. The filtrate was concentrated and then purified by flash chromatography to yield 1-(4-fluoro-phenyl)-4-iodo-2-methyl-1H-imidazole (120 mg, 0.40 mmol, 41%).

Workup

  1. customoxygen was bubbled through the reaction mixture for 40 min
  2. filtrationfiltrated over dicalit
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ee5c1e0fe79a49fc811d570590f99883
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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