Phosphorus trichloride → 4-[5-(4-Fluorophenyl)-1-methyl-2-phenyl-1h-imidazol-4-yl]pyridin-2(1h)-one

HRID 23526Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N+:10]([O-])[C:9]=2[C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][C:9]=2[C:21]2[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one of Step A (56 mg, 0.155 mmol) in CHCl3 (2 mL) was added phosphorous trichloride (16 μL, 0.186 mmol) dropwise at room temperature. The reaction mixture was heated at 60° C. for 2 hours, cooled, and poured into 1N NaOH/ice solution. The aqueous layer was extracted with CH2Cl2, and the combined organic extracts were washed with H2O followed by brine. After drying over Na2SO4, the solvent was removed in vacuo. The crude material was purified by preparative thin layer chromatography (1:10 MeOH:CH2Cl2 as an eluent) to obtain 21.8 mg of the title compound.

Workup

temperaturecooled
extractionThe aqueous layer was extracted with CH2Cl2
washthe combined organic extracts were washed with H2O
dry with materialAfter drying over Na2SO4
customthe solvent was removed in vacuo
customThe crude material was purified by preparative thin layer chromatography (1:10 MeOH

Sources & evidence

ORD record: ord-d536d149bf6e440b94ffa5ef2b01369e
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852727B2

Reaction notes

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