Sodium Thiosulfate → Methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

HRID 245166Notes

Reaction equation

HRID 245166 reaction equation
C(S[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([O:29][CH3:30])=[O:28])C.Cl[C:32]1C=C(C=C[CH:41]=1)C(OO)=O.C([O-])(O)=O.[Na+].[O-:47][S:48]([O-:51])(=S)=O.[Na+].[Na+]>ClCCl>[CH2:32]([S:48]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=1)[C:8]([CH3:26])=[C:7]2[C:27]([O:29][CH3:30])=[O:28])(=[O:51])=[O:47])[CH3:41]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67418873Methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 67384351Methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (7.05 g, 11.33 mmol) and 3-chloroperoxybenzoic acid (5.11 g, 22.78 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous NaHCO3 and Na2S2O3 were added slowly. The mixture was stirred for 30 min and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride) to give methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.4 g, 64% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.98-8.05 (m, 2H), 7.92 (d, J=8.03 Hz, 1H), 7.76-7.85 (m, 2H), 4.10 (s, 3H), 4.09 (s, 3H), 3.54 (q, J=7.53 Hz, 2H), 2.37 (s, 3H), 1.15 (t, J=7.40 Hz, 3H); MS (m/z) 468.1 (M+H+).

Workup

  1. extractionextracted with methylene chloride (three times)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-0a3bd9487a80473d94286eb3092c1680
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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