Tetrahydrofuran → HCID 67383892, compound

HRID 245215Notes

Reaction equation

HRID 245215 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:25]([O:27][CH3:28])=[O:26])=[C:9]([CH3:24])[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[N:11]2)=[CH:6][C:5]=1SCC)[CH3:2].O[O:33][S:34]([O-:36])=O.[K+].O1CC[CH2:40][CH2:39]1>O>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:25]([O:27][CH3:28])=[O:26])=[C:9]([CH3:24])[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[CH:15]=3)=[N:11]2)=[CH:6][C:5]=1[S:34]([CH2:39][CH3:40])(=[O:36])=[O:33])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 67383868HCID 67383868, compound

Product 1

HCID 67383892HCID 67383892, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of methyl 7-(ethyloxy)-6-(ethylthio)-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (10.32 g, 22.95 mmol) in tetrahydrofuran (150 mL) was added oxone (35.3 g, 57.4 mmol) in water (75 mL). The resulting mixture was stirred overnight at room temperature. The mixture was diluted with water and extracted with methylene chloride. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride) to give methyl 7-(ethyloxy)-6-(ethylsulfonyl)-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.11 g, 82% yield). 1H NMR (400 MHz, DMSO-d6) δ8.24 (s, 1H), 7.98-8.05 (m, 2H), 7.92 (d, J=7.78 Hz, 1H), 7.76-7.82 (m, 2H), 4.39 (q, J=6.94 Hz, 2H), 4.09 (s, 3H), 3.56 (q, J=7.28 Hz, 2H), 2.36 (s, 3H), 1.45 (t, J=6.90 Hz, 3H), 1.14 (t, J=7.40 Hz, 3H); MS (m/z) 482.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-caf3e8c8a0f0456eac1492a0a8ca5d1e
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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