Sodium hydride → HCID 178516808, compound

HRID 449952Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11](=[N:14][NH2:15])[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[N:9]1.[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:15][N:14]=[C:11]2[C:12](=[O:13])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:9]=[C:10]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1,3-Bis(2-fluorophenyl)-1H-pyrazole-4,5-dione-4-hydrazone (57 mg, 0.19 mmol) and 4-iodobenzylbromide (56 mg, 0.19 mmol, 1.0 equiv) were dissolved in degassed N,N-dimethylformamide (3 mL), cooled to 0° C. and treated with sodium hydride (17 mg, 0.43 mmol, 2.2 equiv). After stirring at 0° C. for 1.5 hours, the mixture was treated with ammonium chloride (3 mL, aqueous saturated), poured into water (15 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 1:1; hexanes:ethyl acetate), providing the titled compound as a light yellow solid.

Workup

extractionextracted with ethyl acetate (2×50 mL)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel gradient chromatography (100:0 to 1:1; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-8a34b294180d4ff2aa4a4c324b6f3033
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486946B2

Reaction notes

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