Acetic Acid → 1-(2,3'-Difluoro-5-methoxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonyl chloride

HRID 1504404Notes

Reaction equation

C(S[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)=[C:21]([F:34])[CH:20]=1)[C:14](=[O:35])[CH:13]=[CH:12]2)C1C=CC=CC=1.C(Cl)Cl.C(O)(=O)C.[S:43]([Cl:47])(Cl)(=[O:45])=[O:44]>O>[F:34][C:21]1[CH:20]=[C:19]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([S:43]([Cl:47])(=[O:45])=[O:44])=[CH:18][CH:17]=3)[CH:12]=[CH:13][C:14]2=[O:35])[C:24]([O:25][CH3:26])=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A RBF cooled to 0° C., was charged with 6-(benzylthio)-1-(2,3′-difluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinolin-2(1H)-one (0.168 g, 0.346 mmol), DCM (3.30 ml), Acetic Acid (0.082 ml), and Water (0.082 ml). After stirring for 5 minutes at 0° C., sulfuryl chloride (0.028 ml, 0.346 mmol) was added and stirring was continued for an additional 1 hour at 0° C. The reaction was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 1-(2,3′-difluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonyl chloride (0.135 g, 0.292 mmol, 84% yield). m/z (ESI) 462.0 (M+H)+.

Workup

stirringstirring
waitwas continued for an additional 1 hour at 0° C
concentrationThe reaction was concentrated
dissolutiondissolved in minimal DCM
custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane)

Sources & evidence

ORD record: ord-904ba163a4654ead8a19cf3799b21c75
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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