Sodium Iodide → 2-Fluoro-4-[(6-methoxy-7-(3-morpholinopropyl)-4-quinolyl)oxy]aniline

HRID 31152

Reaction equation

[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([CH2:22][CH2:23][CH2:24]Cl)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:26](=[O:29])([O-])[O-].[K+].[K+].[I-].[Na+].FC1C=CC([CH2:41][C:42](O)=O)=CC=1.[CH3:45][N:46](C)C=O>C(Cl)(Cl)Cl.CO>[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([CH2:22][CH2:23][CH2:24][N:46]4[CH2:45][CH2:26][O:29][CH2:42][CH2:41]4)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

Conditions

Temperature: 70 °C

Procedure

The aniline compound (0.7 g) prepared in step 1) was dissolved in dimethylformamide (40 ml) to prepare a solution. Potassium carbonate (1.4 g), sodium iodide (0.6 g) and moripholine (0.85 g) (starting compound B) were added to the solution, and the mixture was stirred at 70° C. for 20 hr. The reaction solution was extracted with ethyl acetate, followed by washing with saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under the reduced pressure. The residue was purified by column chromatography on silica gel, and the title compound (0.64 g, yield 76%) was obtained from the fraction of chloroform:methanol (95:5).

Workup

customto prepare a solution
extractionThe reaction solution was extracted with ethyl acetate
washby washing with saturated brine
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was removed by evaporation under the reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-84cc826f0b834b4a8d693567a5418566
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425564B2

Linked notes

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