Dimethyl Sulfide → 3-Amino-4-(3-fluorophenyl)-6-methoxyquinoline-2-(1H)-one

HRID 1169695Notes

Reaction equation

HRID 1169695 reaction equation
[NH2:1][C:2]1[C:3](=[O:32])[N:4](CC2C=CC(OC)=CC=2OC)[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[CH:9][C:8]([O:19][CH3:20])=[CH:7][CH:6]=2.CSC>FC(F)(F)C(O)=O>[NH2:1][C:2]1[C:3](=[O:32])[NH:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[CH:9][C:8]([O:19][CH3:20])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 588522503-Amino-1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxyquinolin-2-(1H)-one

Product 1

HCID 588522543-Amino-4-(3-fluorophenyl)-6-methoxyquinoline-2-(1H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3-amino-1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxyquinolin-2-(1H)-one (62 mg, 0.143 mmol) in 3 mL of trifluoroacetic acid was added dimethyl sulfide (0.30 mL). After stirring for 2 days, the reaction was heated to reflux for 3 hours, then concentrated in vacuo. The crude residue was purified by flash chromatography through SiO2 (1-3% MeOH/CH2Cl2) to provide the titled product as a yellow solid. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C16H13FN2O2 (M+H+): 285.1034. Found 285.1029.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by flash chromatography through SiO2 (1-3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3fd066e5e62a442880bfaee480f939f1
Source dataset
uspto-grants-2010_11
Patent number
US07825131B2

Reaction notes

Loading…