Potassium Carbonate → Trifluoromethanesulfonic Acid 7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yl Ester

HRID 2266448Notes

Reaction equation

ClC1C=C(O)C2C(C)=C(CC3C=CC(Cl)=CC=3)C(C)=NC=2C=1.ClC1C=C(O)C=C2C=1C(C)=C(CC1C=CC(Cl)=CC=1)C(C)=N2.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:72][C:73]1[CH:82]=[C:81]([O:83][S:84]([C:87]([F:90])([F:89])[F:88])(=[O:86])=[O:85])[CH:80]=[C:79]2[C:74]=1[C:75]([CH3:100])=[C:76]([CH2:92][C:93]1[CH:98]=[CH:97][C:96]([Cl:99])=[CH:95][CH:94]=1)[C:77]([CH3:91])=[N:78]2>O1CCCC1>[Cl:72][C:73]1[CH:74]=[C:79]2[C:80]([C:75]([CH3:100])=[C:76]([CH2:92][C:93]3[CH:98]=[CH:97][C:96]([Cl:99])=[CH:95][CH:94]=3)[C:77]([CH3:91])=[N:78]2)=[C:81]([O:83][S:84]([C:87]([F:89])([F:90])[F:88])(=[O:85])=[O:86])[CH:82]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 7-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol and 5-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-7-ol (0.66 g), N-phenyltrifluoromethanesulfonimide (0.86 g), potassium carbonate (0.82 g) and tetrahydrofuran (10 mL) was heated by microwave irradiation at 130° C. for 20 minutes. The mixture was filtered and the filtrate concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with 1,2-dichloroethane gave a 50:50 mixture of title compound and trifluoromethanesulfonic acid 5-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-7-yl ester as a honey coloured gum, 0.86 g.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate concentrated under reduced pressure
customPurification of the residue by column chromatography on silica gel
washeluting with 1,2-dichloroethane
customgave

Sources & evidence

ORD record: ord-1a6334b0f3044ab198c2a4144dd70497
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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