Water → Perfluorophenyl 1-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

HRID 1504492Notes

Reaction equation

HRID 1504492 reaction equation
C([S:8][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]([Cl:34])[CH:20]=1)[C:14](=[O:35])[CH:13]=[CH:12]2)C1C=CC=CC=1.ClN1C(C)(C)C(=O)N(Cl)C1=[O:39].[F:47][C:48]1[C:53]([F:54])=[C:52]([F:55])[C:51]([F:56])=[C:50]([F:57])[C:49]=1[OH:58].C(N(CC)CC)C.[OH2:66]>C(O)(=O)C.C(Cl)Cl>[Cl:34][C:21]1[CH:20]=[C:19]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([S:8]([O:58][C:49]4[C:48]([F:47])=[C:53]([F:54])[C:52]([F:55])=[C:51]([F:56])[C:50]=4[F:57])(=[O:39])=[O:66])=[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

8

Reactant 5

HCID 962Water2×HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 1177370126-(benzylthio)-1-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)quinolin-2(1H)-one

Product 1

HCID 117737251Perfluorophenyl 1-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonateYield 48.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A RBF was charged with 6-(benzylthio)-1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinolin-2(1H)-one (1.00 g, 1.992 mmol), DCM (18.9 ml), acetic acid (0.47 ml), and water (0.47 ml) to give clear, orange solution. The flask was cooled in an ice-water bath for 10 min, then 1,3-dichloro-5,5-dimethylhydantoin (0.654 ml, 4.98 mmol) was added in one portion. After 30 min, 2,3,4,5,6-pentafluorophenol (0.417 ml, 3.98 mmol) and triethylamine (0.694 ml, 4.98 mmol) (dropwise) were added in sequence. After 2 hours, the mixture was diluted with water, then extracted with DCM (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 25-g silica gel loading column, 0-50% EtOAc/Heptane) to give perfluorophenyl 1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (0.600 g, 0.959 mmol, 48.1% yield) as an off-white solid. m/z (ESI) 626.1 (M+H)+.

Workup

  1. customto give clear
  2. temperatureThe flask was cooled in an ice-water bath for 10 min
  3. waitAfter 2 hours
  4. extractionextracted with DCM (2×)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 25-g silica gel loading column, 0-50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-4ceb58869c544c27a78a641812631fbc
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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