Cesium carbonate → HCID 59379044, compound

HRID 1893678Notes

Reaction equation

HRID 1893678 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH2:13][CH3:14])[CH:8]=[C:7]2[OH:15].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH2:13][CH3:14])[CH:8]=[C:7]2[O:15][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178477297HCID 178477297, compound

Product 1

HCID 59379044HCID 59379044, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

8-Chloro-2-ethylsulfanyl-quinolin-4-ol (10.26 g, 42.8 mmol) was dissolved in anhydrous dimethylformamide (100 mL). Cesium carbonate (27.9 g, 85.6 mmol) was added, followed by p-methoxybenzyl chloride (8.0 g, 51.36 mmol). The mixture was then heated at 65° C. for 2 hours and then cooled to room temperature and diluted with ethyl acetate. The diluted reaction mixture was washed with brine 2 times, dried over Mg2SO4 and concentrated in vacuo. The residue was recrystallized from EtOAc/Hexanes to afford 8-chloro-2-ethylsulfanyl-4-(4-methoxy-benzyloxy)-quinoline (11.14 g, 67% yield). LCMS found 360.21 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. customThe diluted reaction mixture
  3. washwas washed with brine 2 times
  4. dry with materialdried over Mg2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from EtOAc/Hexanes

Sources & evidence

ORD record
ord-ad2ea7c2c4184cffbdde941b9cfac519
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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