Dimethylformamide → ethyl 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

HRID 39804Notes

Reaction equation

HRID 39804 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14](=[O:32])[N:15]2[CH2:18][CH2:19][CH2:20][C:21]2([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[F:39][C:40]1[CH:41]=[C:42]([S:46][CH2:47][CH2:48]Br)[CH:43]=[CH:44][CH:45]=1>O.C(OCC)(=O)C>[F:39][C:40]1[CH:41]=[C:42]([S:46][CH2:47][CH2:48][N:24]2[CH2:25][CH2:26][C:21]([CH2:20][CH2:19][CH2:18][N:15]3[C:16]4[C:11](=[CH:10][CH:9]=[C:8]([O:7][CH3:6])[CH:17]=4)[CH:12]=[CH:13][C:14]3=[O:32])([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:23]2)[CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 224706261-[(2-Bromoethyl)sulfanyl]-3-fluorobenzeneHCID 59398137ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 59398133ethyl 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylateYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 2.5 mL of an N,N-dimethylformamide solution containing 0.10 g of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 74 mg of potassium carbonate and 69 mg of 1-(3-fluorophenyl)thio-2-bromoethane were added at room temperature, and stirred at 60° C. for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added. The organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1], to give 95 mg of ethyl 1-(2-((3-fluorophenyl)thio)ethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate as a yellow oil.

Workup

  1. additionwere added at room temperature
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. washwashed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-a963f73403514908a18185c1237964e0
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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