Sodium Iodide → {2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethyl}-dimethyl-amine

HRID 228955Notes

Reaction equation

[CH3:1][N:2]([CH3:5])[CH:3]=O.ClC[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([O:20][C:21]3[C:22]([CH3:31])=[N:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O>[CH3:33][O:32][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:10]=1[O:9][CH2:8][CH2:3][N:2]([CH3:5])[CH3:1])[N:17]=[CH:16][CH:15]=[C:14]2[O:20][C:21]1[C:22]([CH3:31])=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2

Participants

Conditions

Temperature: 80 °C

Procedure

N,N-Dimethylformamide (2.5 ml) was added to 7-(2-chloro-ethoxy)-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (compound 353) (100 mg), potassium carbonate (500 mg), sodium iodide (20 mg), and water (0.05 ml), and the mixture was stirred at 80° C. for 3 days. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (34.2 mg, yield 33%).

Workup

customThe solvent was removed by distillation under the reduced pressure, water
additionwas added to the residue
extractionthe mixture was extracted with chloroform
washThe chloroform layer was washed with water
dry with materialwas then dried over anhydrous sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-cb3e98300b9847bab766862719aa798f
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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