Pyridine → Tert-butyl 4-[1-(2-fluorophenyl)-imidazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 2267142Notes

Reaction equation

HRID 2267142 reaction equation
N1C=CC=CC=1.[NH:7]1[CH:11]=[C:10]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=2)[N:9]=[CH:8]1.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1OB(O)O>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:7]1[CH:11]=[C:10]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=2)[N:9]=[CH:8]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 222378312-Fluorophenylboric acidHCID 178451779tert-butyl 4-(1H-imidazol-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylate

Product 1

HCID 58945849Tert-butyl 4-[1-(2-fluorophenyl)-imidazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Copper acetate (35 mg) and pyridine (0.02 ml) were added to a solution of 2 mg of the compound prepared in the above 3), i.e. tert-butyl 4-(1H-imidazol-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylate and 35 mg of 2-fluorophenylboric acid in dichloromethane and the solution was stirred for three days. The solvent was evaporated in vacuo and the residue was separated and purified by a thin-layer chromatography (ethyl acetate/hexane=1/2) to give 2.48 mg of the title compound as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was separated
  3. custompurified by a thin-layer chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-6fab518853ea430890c082b2cd7c838a
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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