Sodium hydride → ethyl 4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydrocinnoline-3-carboxylate

HRID 241997Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:17])[C:9](=[N:15][NH2:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[O:17]=[C:8]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=2)[N:16]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:24][CH:25]=2)[N:15]=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 3-(2-fluorophenyl)-2-hydrazono-3-oxopropanoate (1.16 g, 4.87 mmol) and 1-[4-(bromomethyl)phenyl]-1H-pyrazole (1.50 g, 6.33 mmol, 1.3 equiv) were dissolved in degassed N,N-dimethylformamide (15 mL), cooled to 0° C. and treated with sodium hydride (0.312 g, 7.79 mmol, 1.6 equiv). After stirring for 1 hour at 0° C., the mixture was treated with ammonium chloride (3 mL, saturated aqueous) and water (40 mL) and extracted with ethyl acetate (3×75 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 20:80; hexanes:ethyl acetate) to provide the titled compound.

Workup

extractionextracted with ethyl acetate (3×75 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 20:80; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-7c1c8a958c7845cd88936c6ac7001ba3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653079B2

Reaction notes

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