2-Chloro-5-fluoropyridine → 4-(5-Fluoro-2-pyridyl)-1-trityl-1H-imidazole

HRID 431984Notes

Reaction equation

HRID 431984 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)CCC.Cl[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][N:40]=1>C1(C)C=CC=CC=1>[F:45][C:42]1[CH:43]=[CH:44][C:39]([C:6]2[N:7]=[CH:8][N:9]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:10]=2)=[N:40][CH:41]=1

Participants

4

Reactant 2

HCID 27828012-Chloro-5-fluoropyridineHCID 118281174-(Tributylstannyl)-1-tritylimidazole

Product 1

HCID 219424474-(5-Fluoro-2-pyridyl)-1-trityl-1H-imidazoleYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 4-Tributylstannyl-1-trityl-1H-imidazole (1.00 g, 1.67 mmol) in toluene (10 ml) added 2-Chloro-5-fluoropyridine (0.31 g, 2.38 mmol) and tetrakis(triphenylphoshine)palladium (0) (0.19 g, 0.17 mmol), sequentially. The resulting brownish yellow reaction mixture was heated at reflux under argon overnight. The reaction mixture was cooled to room temperature and concentrated in-vacuo. The residue was purified on silica gel using 30% diethyl ether in hexanes to isolate 4-(5-Fluoro-2-pyridyl)-1-trityl-1H-imidazole (0.23 g) as a clear oil.

Workup

  1. temperatureThe resulting brownish yellow reaction mixture was heated
  2. temperatureat reflux under argon overnight
  3. concentrationconcentrated in-vacuo
  4. customThe residue was purified on silica gel using 30% diethyl ether in hexanes

Sources & evidence

ORD record
ord-ddcfbe05e74f4554b532bafb89cc1472
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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