Potassium Carbonate → HCID 22063513, compound

HRID 1828553Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:26])[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][NH:18]3)=[CH:13][CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35][F:36]>CN(C)C=O.C(OCC)(=O)C>[F:36][CH2:35][CH2:34][N:18]1[C:19]2[C:14](=[CH:13][CH:12]=[C:11](/[CH:10]=[CH:9]/[C:6]3[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)[CH:20]=2)[C:15](=[O:26])[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17]1

Participants

Conditions

Temperature: 65 °C

Procedure

Ethyl 7-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate (368 mg, 1.00 mmol) was dissolved in dimethylformamide (6 ml), added with potassium carbonate (276 mg, 2.00 mmol) and 1-bromo-2-fluoroethane (0.223 ml, 3.00 mmol), and then the mixture was stirred overnight at 65° C. The reaction mixture was left stand for cooling and then diluted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1) to obtain the title compound (254 mg, 61%) as colorless transparent oil.

Workup

waitThe reaction mixture was left stand
temperaturefor cooling
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=100:1)

Sources & evidence

ORD record: ord-2b30ea3392674aa99f0f708a6d8948ab
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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