Dimethyl Sulfide → 4-(3-Fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 640717Notes

Reaction equation

HRID 640717 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:8]([C:25]#[N:26])[C:7]1=[O:27].CSC>ClCCl.FC(F)(F)C(O)=O>[F:24][C:20]1[CH:19]=[C:18]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)[NH:6][C:7](=[O:27])[C:8]=2[C:25]#[N:26])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 1068Dimethyl SulfideHCID 112707271-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Product 1

HCID 114151654-(3-Fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (42 mg, 0.094 mmol) in 0.5 mL of dichloromethane and 1 mL of trifluoroacetic acid was added dimethyl sulfide (0.10 mL). After stirring for 2 days, the reaction was heated to reflux for 10 hours, then concentrated in vacuo. The crude product was triturated with EtOAc to provide the titled product as a pale yellow solid. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C17H11FN2O2 (M+H+): 295.0878. Found 295.0879.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 10 hours
  3. concentrationconcentrated in vacuo
  4. customThe crude product was triturated with EtOAc

Sources & evidence

ORD record
ord-26ad575b58114d2a8551c9322c23122d
Source dataset
uspto-grants-2010_04
Patent number
US07692017B2

Reaction notes

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